Nicotinic acid, hydrazide → 2-Methyl-1-{[5-(3-pyridinyl)-1,3,4-oxadiazol-2-yl]methyl}-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 913516Notes

Reaction equation

HRID 913516 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].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([NH:29][NH2:30])=O)[CH:22]=1>>[CH3:16][C:7]1[N:8]([CH2:12][C:13]2[O:15][C:27]([C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)=[N:29][N:30]=2)[C:9]2[C:5]([CH:6]=1)=[C:4]([C:17]([F:19])([F:18])[F:20])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=2

Participants

3

Reactant 2

HCID 11112Nicotinic acid, hydrazideHCID 67404858[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid

Product 1

HCID 674049522-Methyl-1-{[5-(3-pyridinyl)-1,3,4-oxadiazol-2-yl]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 3-pyridinecarbohydrazide: 1H NMR (400 MHz, DMSO-d6) δ 9.08 (s, 1H), 8.78 (d, J=4.9 Hz, 1H), 8.27 (d, J=7.8 Hz, 1H), 8.08 (d, J=8.5 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.60 (dd, J=7.8 and 4.9 Hz, 1H), 6.65 (s, 1H), 6.00 (s, 2H), 2.57 (s, 3H); MS (ES) m/z 384 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-8ef9d089f01b4ed6b41145218ba1fafb
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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