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-methyl-1H-indole-5-carbonitrile

HRID 913608Notes

Reaction equation

HRID 913608 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.Cl[CH2:15][C:16]1[N:20]=[C:19]([C:21]2[C:22]([CH3:27])=[N:23][O:24][C:25]=2[CH3:26])[O:18][N:17]=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]([CH3:13])[N:6]2[CH2:15][C:16]1[N:20]=[C:19]([C:21]2[C:22]([CH3:27])=[N:23][O:24][C:25]=2[CH3:26])[O:18][N:17]=1

Participants

3

Reactant 2

HCID 27357603-(Chloromethyl)-5-(3,5-dimethylisoxazol-4-yl)-1,2,4-oxadiazoleHCID 674048784-chloro-2-methyl-1H-indole-5-carbonitrile

Product 1

HCID 578001224-Chloro-1-{[5-(3,5-dimethyl-4-isoxazolyl)-1,2,4-oxadiazol-3-yl]methyl}-2-methyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-methyl-1H-indole-5-carbonitrile and 3-(chloromethyl)-5-(3,5-dimethyl-4-isoxazolyl)-1,2,4-oxadiazole: 1H NMR (400 MHz, DMSO-d6) δ 7.93 (s, 1 H), 7.81 (d, J=8.5 Hz, 1 H), 7.58 (d, J=8.5 Hz, 1 H), 5.81 (s, 2 H), 3.30 (s, 3 H), 2.66 (s, 3 H), 2.39 (s, 3 H); MS (ES) m/z 368 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-9e84b492405f4a8b9ee9837541ff1172
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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