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-propyl-1H-indole-5-carbonitrile

HRID 913602Notes

Reaction equation

HRID 913602 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]([CH2:13][CH2:14][CH3:15])[NH:6]2.[F:16][C:17]([F:36])([F:35])[C:18]1[CH:19]=[C:20]([C:28]2[O:32][N:31]=[C:30]([CH2:33]Cl)[N:29]=2)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>>[F:36][C:17]([F:16])([F:35])[C:18]1[CH:19]=[C:20]([C:28]2[O:32][N:31]=[C:30]([CH2:33][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[CH2:13][CH2:14][CH3:15])[N:29]=2)[CH:21]=[C:22]([C:24]([F:26])([F:25])[F:27])[CH:23]=1

Participants

3

Reactant 2

HCID 27809575-[3,5-Bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazoleHCID 674043384-chloro-2-propyl-1H-indole-5-carbonitrile

Product 1

HCID 578003981-({5-[3,5-bis(Trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-4-chloro-2-propyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-propyl-1H-indole-5-carbonitrile and 5-[3,5-bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazole: 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 2 H), 8.50 (s, 1 H), 7.96 (s, 1 H), 7.77 (d, J=8.7 Hz, 1 H), 7.59 (d, J=8.7 Hz, 1 H), 5.87 (s, 2 H), 2.97-2.82 (m, 2 H), 1.70-1.56 (m, 2 H), 0.97-0.89 (m, 3 H); MS (ES) m/z 513 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-db9ab2987b63447c94a4f6321212d546
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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