4-Fluorobenzohydrazide → 1-{[5-(4-Fluorophenyl)-1,3,4-oxadiazol-2-yl]methyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 913519Notes

Reaction equation

HRID 913519 reaction equation
[C:1]([C:3]1[C:4]([C:17]([F:20])([F:19])[F:18])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([OH:15])=O)[C:7]([CH3:16])=[CH:6]2)#[N:2].[F:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([NH:28][NH2:29])=O)=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]2[O:15][C:13]([CH2:12][N:8]3[C:9]4[C:5](=[C:4]([C:17]([F:20])([F:18])[F:19])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=4)[CH:6]=[C:7]3[CH3:16])=[N:29][N:28]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 99724-FluorobenzohydrazideHCID 67404858[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid

Product 1

HCID 674050251-{[5-(4-Fluorophenyl)-1,3,4-oxadiazol-2-yl]methyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 35C using [5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid and 4-fluorobenzohydrazide: 1H NMR (400 MHz, DMSO-d6) δ 8.07 (d, J=8.4 Hz, 1H), 7.96 (dd, J=8.7 and 5.4 Hz, 2H), 7.77 (d, J=8.4 Hz, 1H), 7.41 (t, J=8.7 Hz, 2H), 6.65 (s, 1H), 5.97 (s, 2H), 2.57 (s, 3H); MS (ES) m/z 401 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-4fc87c24460d4ee2b2d8643598c5861d
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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