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-methyl-1H-indole-5-carbonitrile

HRID 913607Notes

Reaction equation

HRID 913607 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]([CH3:13])[NH:6]2.[F:14][C:15]([F:34])([F:33])[C:16]1[CH:17]=[C:18]([C:26]2[O:30][N:29]=[C:28]([CH2:31]Cl)[N:27]=2)[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1>>[F:34][C:15]([F:14])([F:33])[C:16]1[CH:17]=[C:18]([C:26]2[O:30][N:29]=[C:28]([CH2:31][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[CH3:13])[N:27]=2)[CH:19]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:21]=1

Participants

3

Reactant 2

HCID 27809575-[3,5-Bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazoleHCID 674048784-chloro-2-methyl-1H-indole-5-carbonitrile

Product 1

HCID 579206091-({5-[3,5-bis(Trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-4-chloro-2-methyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-methyl-1H-indole-5-carbonitrile 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), 8.49 (s, 1 H), 7.94 (s, 1 H), 7.83 (d, J=8.5 Hz, 1 H), 7.60 (d, J=8.7 Hz, 1 H), 5.87 (s, 2 H), 2.51 (s, 3 H); MS (ES) m/z 485 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-c95410996be043b6b78840ad660e4321
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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