5-[3,5-Bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazole → 1-({5-[3,5-bis(Trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-4-chloro-2-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 913613Notes

Reaction equation

HRID 913613 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([F:16])([F:15])[F:14])[NH:6]2.[F:17][C:18]([F:37])([F:36])[C:19]1[CH:20]=[C:21]([C:29]2[O:33][N:32]=[C:31]([CH2:34]Cl)[N:30]=2)[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1>>[F:37][C:18]([F:17])([F:36])[C:19]1[CH:20]=[C:21]([C:29]2[O:33][N:32]=[C:31]([CH2:34][N:6]3[C:7]4[C:3](=[C:2]([Cl:1])[C:10]([C:11]#[N:12])=[CH:9][CH:8]=4)[CH:4]=[C:5]3[C:13]([F:14])([F:15])[F:16])[N:30]=2)[CH:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:24]=1

Participants

3

Reactant 2

HCID 27809575-[3,5-Bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazoleHCID 674056604-chloro-2-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 578001071-({5-[3,5-bis(Trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-4-chloro-2-(trifluoromethyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 228B) and 5-[3,5-bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazole: 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 2 H), 8.51 (s, 1 H), 8.03-7.95 (m, 1 H), 7.94-7.86 (m, 1 H), 7.52 (s, 1 H), 5.99 (s, 2 H); MS (ES) m/z 539 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-a4ccfd96f10e4303ae478bdd7309789e
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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