4-(Trifluoromethyl)pyridine-2-carboxylic acid → 2-Cyclopropyl-4-(trifluoromethyl)-1-({5-[4-(trifluoromethyl)-2-pyridinyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-indole-5-carbonitrile

HRID 913760Notes

Reaction equation

HRID 913760 reaction equation
[C:1]([C:3]1[C:4]([C:20]([F:23])([F:22])[F:21])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13](=[NH:16])[NH:14][OH:15])[C:7]([CH:17]1[CH2:19][CH2:18]1)=[CH:6]2)#[N:2].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([C:32](O)=O)[CH:27]=1>>[CH:17]1([C:7]2[N:8]([CH2:12][C:13]3[N:16]=[C:32]([C:28]4[CH:27]=[C:26]([C:25]([F:35])([F:24])[F:36])[CH:31]=[CH:30][N:29]=4)[O:15][N:14]=3)[C:9]3[C:5]([CH:6]=2)=[C:4]([C:20]([F:22])([F:23])[F:21])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=3)[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 120251644-(Trifluoromethyl)pyridine-2-carboxylic acidHCID 178509470HCID 178509470, compound

Product 1

HCID 866207192-Cyclopropyl-4-(trifluoromethyl)-1-({5-[4-(trifluoromethyl)-2-pyridinyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 72 from 2-[5-cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (Example 364B) and 4-(trifluoromethyl)-2-pyridinecarboxylic acid: 1H NMR (400 MHz, CDCl3) δ 9.01 (d, J=4.7 Hz, 1H), 8.33 (s, 1H), 7.75 (d, J=4.7 Hz, 1H), 7.68 (d, J=8.5 Hz 1H), 7.56 (d, J=8.5 Hz 1H), 6.49 (s, 1H), 5.70 (s, 2H), 2.14 (m, 1H), 1.16 (m, 2H), 0.90 (m, 2H); MS (ES) m/z 478 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-19034885025b4ee9901d1528187011b5
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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