4-(Bromomethyl)-1,2-difluorobenzene → (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-1-(3,4-difluorobenzyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetic acid
Reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[NH:19][CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[F:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:33]Br>>[C:1]([O:5][C@@H:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[N:19]([CH2:33][C:32]3[CH:35]=[CH:36][C:37]([F:38])=[C:30]([F:29])[CH:31]=3)[CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in a manner similar to that described in Example 2 from methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate and 3,4-difluorobenzyl bromide. The crude racemic mixture was purified by chiral chromatography to give (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-1-(3,4-difluorobenzyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetic acid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.68-7.59 (m, 1H), 7.52-7.45 (m, 1H), 7.46-7.39 (m, 1H), 7.17-6.98 (m, 4H), 6.06-5.99 (m, 1H), 5.86-5.71 (m, 1H), 5.38-5.32 (s, 1H), 3.64 (s, 3H), 1.02 (s, 9H); LCMS (m/z) ES+=515 (M+1).
Workup
- customThe title compound was prepared in a manner similar to
- customThe crude racemic mixture was purified by chiral chromatography
Sources & evidence
- ORD record
- ord-c3046c2c52ce4fd19808025d6742522c
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012642B2
Reaction notes
Loading…