2-Bromoacetamide → 2-[5-Cyano-2-(2-methylpropyl)-4-(trifluoromethyl)-1H-indol-1-yl]acetamide

HRID 2101989Notes

Reaction equation

HRID 2101989 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2.Br[CH2:21][C:22]([NH2:24])=[O:23]>>[C:17]([C:9]1[C:10]([C:13]([F:16])([F:14])[F:15])=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([CH2:21][C:22]([NH2:24])=[O:23])[C:4]([CH2:3][CH:2]([CH3:19])[CH3:1])=[CH:12]2)#[N:18]

Participants

3

Reactant 2

HCID 696322-BromoacetamideHCID 674051962-(2-methylpropyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 674062162-[5-Cyano-2-(2-methylpropyl)-4-(trifluoromethyl)-1H-indol-1-yl]acetamide

Procedure

Synthesized as described in Example 4 using 2-(2-methylpropyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile and 2-bromoacetamide: 1H NMR (400 MHz, DMSO-d6) δ 7.82 (d, J=8.5 Hz, 1H), 7.71 (bs, 1H), 7.67 (d, J=8.5 Hz, 1H), 7.34 (bs, 1H), 6.51 (d, J=2.2 Hz, 1H), 4.91 (s, 2H), 2.61 (d, J=7.0 Hz, 2H), 1.95 (m, 1H), 0.92 (d, J=6.6 Hz, 6H); MS (ES) m/z 324 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-49c69c52cc764ed98907ee16b3452aef
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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