[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid → 2-Methyl-4-(trifluoromethyl)-1-({3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}methyl)-1H-indole-5-carbonitrile

HRID 913512Notes

Reaction equation

HRID 913512 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)[C:7]([CH3:16])=[CH:6]2)#[N:2].[OH:21][NH:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=1)=[NH:24]>>[CH3:16][C:7]1[N:8]([CH2:12][C:13]2[O:21][N:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:32])[F:34])[CH:26]=3)[N:24]=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 67404858[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acidHCID 178513295HCID 178513295, compound

Product 1

HCID 866206672-Methyl-4-(trifluoromethyl)-1-({3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}methyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 37 using [5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid and N-hydroxy-3-(trifluoromethyl)benzenecarboximidamide: 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.20 (d, J=7.8 Hz, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.60 (m, 3H), 6.69 (s, 1H), 5.60 (s, 2H), 2.65 (s, 3H); MS (ES) m/z 473 (M+Na).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-f90610fbf6fc452db8988c6234952422
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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