4-(Bromomethyl)-1,2-difluorobenzene → 2-Tert-butoxy-2-[1-[(3,4-difluorophenyl)methyl]-6-methyl-7-oxo-4-(p-tolyl)pyrrolo[2,3-c]pyridin-5-yl]acetic acid

HRID 1473216Notes

Reaction equation

HRID 1473216 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]([CH3:28])=[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][CH: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:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 89462627methyl 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

Product 1

HCID 715370612-Tert-butoxy-2-[1-[(3,4-difluorophenyl)methyl]-6-methyl-7-oxo-4-(p-tolyl)pyrrolo[2,3-c]pyridin-5-yl]acetic acid

Procedure

The title compound was prepared in two steps in a manner similar to that described in Example 27 step D from methyl 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate and 3,4-difluorobenzyl bromide, and was isolated as white solid after reverse phase chromatography (46%): 1H NMR (400 MHz, CHLOROFORM-d) ppm 0.98 (s, 9H), 2.43 (s, 3H), 3.66 (s, 3H), 5.45 (s, 1H), 5.68-5.86 (m, 2H), 6.06 (d, J=2.8 Hz, 1H), 6.97-7.05 (m, 2H), 7.05-7.15 (m, 2H), 7.25-7.31 (m, 2H), 7.31-7.38 (m, 1H), 7.49-7.59 (m, 1H); LCMS (m/z) ES+=495 (M+1).

Workup

  1. customwas isolated as white solid after reverse phase chromatography (46%)

Sources & evidence

ORD record
ord-4986a9f8955547208b189de4e80cf57f
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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