US2004176614A1PendingUtilityA1
Process for the preparation of indole derivatives and intermediates of the process
Priority: May 26, 2000Filed: Mar 18, 2004Published: Sep 9, 2004
Est. expiryMay 26, 2020(expired)· nominal 20-yr term from priority
C07D 209/30C07D 209/24
49
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Claims
Abstract
A process for the preparation of compounds of formula wherein R 1 is C 1 -C 6 alkyl and X is hydrogen, a hydrocarbon radical or a cation, wherein a compound of formula wherein R 1 is as defined above and R 2 is hydrogen or a hydrocarbon radical, is reduced, the resulting compound of formula is reacted with a compound that introduces the radical of formula —CH 2 —COOR 3 , wherein R 3 has the meanings given above for R 2 , and the resulting compound of formula is reduced and optionally hydrolysed.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A process for the preparation of a compound of formula
wherein R 1 is C 1 -C 6 alkyl and
X is hydrogen, a hydrocarbon radical or a cation,
wherein a compound of formula
wherein R 1 is as defined above and R 2 is hydrogen or a hydrocarbon radical, is reduced, the resulting compound of formula
wherein R 1 and R 2 are as defined above, is reacted with a compound that introduces the radical of formula —CH 2 —COOR 3 wherein R 3 has the meanings given above for R 2 , and the resulting compound of formula
is reduced and optionally hydrolysed.
2 . A process according to claim 1 , wherein the compound of formula (2) is obtained by reacting a compound of formula
wherein R 1 is as defined in claim 1 and
Y is bromine, chlorine, iodine, —OSO 2 CF 3 or —COCl, especially bromine, with a compound that introduces the radical of formula —CH═CH—Z, wherein
Z is the radical —COOR 4 , —COR 5 or —CN,
R 4 is hydrogen or a hydrocarbon radical and
R 5 is a hydrocarbon radical or unsubstituted or substituted amino,
and reacting the resulting compound of formula
optionally after conversion of the compound of formula (6) wherein Z is the radical —COOR 4 into the corresponding acid chloride or into the free acid,
with a compound that introduces the radical of formula —CH 2 —COOR 2 wherein
R 2 is as defined in claim 1 .
3 . A process according to claim 1 , wherein the compound of formula (2) is obtained by reacting a compound of formula
with a compound of formula CH 3 —CO—CH 2 —COOR 2 and, optionally, then with a compound that introduces a protecting group, to form a compound of formula
wherein R 1 and R 2 are as defined in claim 1 , and
R 8 and R 9 are hydrogen or a protecting group, introducing a double bond under acidic or basic conditions, and removing any protecting group that may be present.
4 . A process according to claim 1 , wherein the compound of formula (2) is obtained by reacting a compound of formula
with a compound of formula
to form a compound of formula
and reacting that compound with a compound that introduces the radical of formula —CH 2 —COOR 2 wherein R 1 and R 2 are as defined in claim 1 ,
R 6 and R 7 are hydrogen or hydrocarbon radicals,
R 11 is C 1 -C 4 alkyl or phenyl, especially methyl or ethyl,
Ph is phenyl and An − is an anion.
5 . A process according to any one of claims 1 to 4 , wherein there is used as compound of formula (3) a compound of formula
wherein R 1 and R 2 are as defined in claim 1 .
6 . A process according to any one of claims 1 to 5 , wherein the compound of formula (4) is hydrolysed.
7 . A process according to any one of claims 1 to 6 , wherein
R 1 is isopropyl.
8 . A process according to any one of claims 1 to 7 , wherein
R 2 , R 3 , R 4 , R 6 and R 7 are C 1 -C 8 alkyl.
9 . A process according to any one of claims 1 to 8 , wherein
R 5 is C 1 -C 6 alkyl or a radical of formula —N(OR 6 )R 7 in which R 6 and R 7 are C 1 -C 6 alkyl.
10 . A process according to any one of claims 3 and 5 to 8 , wherein
R 6 and R 9 are each independently of the other hydrogen, C 1 -C 4 alkylcarbonyl or C 1 -C 4 alkoxy-carbonyl.
11 . A process according to any one of claims 2 and 6 to 9 , wherein
Y is bromine.
12 . A process according to any one of claims 1 to 11 , wherein
X is a cation, especially sodium.
13 . A compound of formula
wherein R 1 is C 1 -C 6 alkyl and
R 2 is hydrogen or a hydrocarbon radical, especially C 1 -C 6 alkyl.
14 . A compound according to claim 13 , wherein
R 1 is isopropyl and R 2 is C 1 -C 6 alkyl.
15 . A process for the preparation of a compound of formula (2) according to claim 13 , wherein a compound of formula
wherein R 1 is as defined in claim 13 and
Y is bromine, chlorine, iodine, —OSO 2 CF 3 or —COCl, especially bromine, is reacted with a compound that introduces the radical of formula —CH═CH—Z, wherein
Z is the radical —COOR 4 , —COR 5 or —CN,
R 4 is hydrogen or a hydrocarbon radical and
R 5 is a hydrocarbon radical or unsubstituted or substituted amino,
and the resulting compound of formula
optionally after conversion of the compound of formula (6) wherein Z is the radical —COOR 4 into the corresponding acid chloride or into the free acid, is reacted with a compound that introduces the radical of formula —CH 2 —COOR 2 wherein
R 2 is as defined in claim 13 .
16 . A process for the preparation of a compound of formula (2) according to claim 13 , wherein a compound of formula
is reacted with a compound of formula CH 3 CO—CH 2 —COOR 2 and, optionally, then with a compound that introduces a protecting group, to form the compound of formula
wherein R 1 and R 2 are as defined in claim 13 and
R 8 and R 9 are hydrogen or a protecting group,
a double bond is introduced under acidic or basic conditions, and any protecting group that may be present is removed.
17 . A process for the preparation of a compound of formula (2) according to claim 13 , wherein a compound of formula
is reacted with a compound of formula
to form the compound of formula
and that compound is reacted with a compound that introduces the radical of formula
—CH 2 —COOR 2 wherein R 1 and R 2 are as defined in claim 13 ,
R 6 and R 7 are hydrogen or hydrocarbon radicals,
R 11 , is C 1 -C 4 alkyl or phenyl, especially methyl or ethyl,
Ph is phenyl and An − is an anion
18 . The use of a compound of formula (2) according to claim 13 as an intermediate in the preparation of a compound of formula (1) according to claim 1 .
19 . A compound of formula
wherein R 1 is C 1 -C 6 alkyl and
R 2 is hydrogen or a hydrocarbon radical, especially C 1 -C 6 alkyl.
20 . A compound according to claim 19 of formula
wherein R 1 and R 2 are as defined in claim 19 .
21 . A compound according to either claim 19 or claim 20 , wherein
R 1 is isopropyl and R 2 is C 1 -C 6 alkyl.
22 . The use of a compound of formula (3) according to claim 19 as an intermediate in the preparation of a compound of formula (1) according to claim 1 .
23 . A compound of formula
wherein R 1 is C 1 -C 6 alkyl, and
R 6 and R 7 are hydrogen or hydrocarbon radicals, especially C 1-6 alkyl.
24 . A compound according to claim 23 , wherein
R 1 is isopropyl and R 6 and R 7 are C 1 -C 6 alkyl.
25 . The use of a compound of formula (8) according to claim 23 as an intermediate in the preparation of a compound of formula (1) according to claim 1 or of a compound of formula (2) according to claim 13 .
26 . A compound of formula
wherein R 1 is C 1 -C 6 alkyl and
Y is bromine, chlorine or iodine, especially bromine.
27 . A compound according to claim 26 , wherein
R 1 is isopropyl and Y is bromine.
28 . The use of a compound of formula (5) according to claim 26 as an intermediate in the preparation of a compound of formula (1) according to claim 1 or of a compound of formula (2) according to claim 13.Join the waitlist — get patent alerts
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