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

HRID 913515Notes

Reaction equation

HRID 913515 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](O)=[O:14])[C:7]([CH3:16])=[CH:6]2)#[N:2].[Br:21][C:22]1[CH:23]=[C:24]([C:28]([NH:30][NH2:31])=O)[CH:25]=[N:26][CH:27]=1>>[Br:21][C:22]1[CH:23]=[C:24]([C:28]2[O:14][C:13]([CH2:12][N:8]3[C:9]4[C:5](=[C:4]([C:17]([F:18])([F:19])[F:20])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=4)[CH:6]=[C:7]3[CH3:16])=[N:31][N:30]=2)[CH:25]=[N:26][CH:27]=1

Participants

3

Reactant 2

HCID 6963655-BromonicotinohydrazideHCID 67404858[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid

Product 1

HCID 674057541-{[5-(5-Bromo-3-pyridinyl)-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 5-bromo-3-pyridinecarbohydrazide: 1H NMR (400 MHz, DMSO-d6) δ 9.05 (d, J=1.7 Hz, 1H), 8.93 (d, J=2.0 Hz, 1H), 8.48 (dd, J=2.0 and 1.7 Hz, 1H), 8.07 (d, J=8.5 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 6.65 (s, 1H), 5.99 (s, 2H), 2.58 (s, 3H); MS (ES) m/z 462 (M+1, isotope for Br) and 464 (M+1, isotope for Br)

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-02b3860ce8014a3ca1b1a89d9f89fe3b
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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