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

HRID 1473221Notes

Reaction equation

HRID 1473221 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]=[C:36]([F:39])[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:31]=[C:30]([F:29])[C:37]([F:38])=[C:36]([F:39])[CH:35]=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 27770623,4,5-Trifluorobenzyl bromideHCID 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 715370572-Tert-butoxy-2-[6-methyl-7-oxo-4-(p-tolyl)-1-[(3,4,5-trifluorophenyl)methyl]pyrrolo[2,3-c]pyridin-5-yl]acetic acid

Procedure

The title compound was prepared 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 3,4,5-trifluorobenzyl bromide, and was isolated as beige solid after reverse phase chromatography (81%): 1H NMR (400 MHz, CHLOROFORM-d) ppm 0.99 (s, 9H), 2.43 (s, 3H), 3.65 (s, 3H), 5.46 (s, 1H), 5.75 (s, 2H), 6.08 (d, J=2.7 Hz, 1H), 6.87 (t, J=7.1 Hz, 2H), 7.01 (d, J=2.7 Hz, 1H), 7.28 (d, 2H), 7.31-7.39 (m, 1H), 7.48-7.57 (m, 1H). LCMS (m/z) ES+=513 (M+1).

Workup

  1. customwas isolated as beige solid after reverse phase chromatography (81%)

Sources & evidence

ORD record
ord-7bd1585aff6847eea2550a2a263d8a26
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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