3-(Chloromethyl)-5-(3,5-dimethylisoxazol-4-yl)-1,2,4-oxadiazole → 4-Chloro-1-{[5-(3,5-dimethyl-4-isoxazolyl)-1,2,4-oxadiazol-3-yl]methyl}-2-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 913614Notes

Reaction equation

HRID 913614 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.Cl[CH2:18][C:19]1[N:23]=[C:22]([C:24]2[C:25]([CH3:30])=[N:26][O:27][C:28]=2[CH3:29])[O:21][N:20]=1>>[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:14])([F:15])[F:16])[N:6]2[CH2:18][C:19]1[N:23]=[C:22]([C:24]2[C:25]([CH3:30])=[N:26][O:27][C:28]=2[CH3:29])[O:21][N:20]=1

Participants

3

Reactant 2

HCID 27357603-(Chloromethyl)-5-(3,5-dimethylisoxazol-4-yl)-1,2,4-oxadiazoleHCID 674056604-chloro-2-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 578004174-Chloro-1-{[5-(3,5-dimethyl-4-isoxazolyl)-1,2,4-oxadiazol-3-yl]methyl}-2-(trifluoromethyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-(trifluoromethyl)-1H-indole-5-carbonitrile and 3-(chloromethyl)-5-(3,5-dimethyl-4-isoxazolyl)-1,2,4-oxadiazole: 1H NMR (400 MHz, DMSO-d6) δ 7.97 (d, J=8.5 Hz, 1 H), 7.87 (d, J=8.5 Hz 1 H), 7.50 (s, 1 H), 5.93 (s, 2H), 2.64 (s, 3H), 2.37 (s, 3H); MS (ES) m/z 422 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-de0e38b94164472da6f3d4c12ba1ba5a
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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