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-propyl-1H-indole-5-carbonitrile

HRID 913604Notes

Reaction equation

HRID 913604 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.Cl[CH2:17][C:18]1[N:22]=[C:21]([C:23]2[C:24]([CH3:29])=[N:25][O:26][C:27]=2[CH3:28])[O:20][N:19]=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]([CH2:13][CH2:14][CH3:15])[N:6]2[CH2:17][C:18]1[N:22]=[C:21]([C:23]2[C:24]([CH3:29])=[N:25][O:26][C:27]=2[CH3:28])[O:20][N:19]=1

Participants

3

Reactant 2

HCID 27357603-(Chloromethyl)-5-(3,5-dimethylisoxazol-4-yl)-1,2,4-oxadiazoleHCID 674043384-chloro-2-propyl-1H-indole-5-carbonitrile

Product 1

HCID 578001124-Chloro-1-{[5-(3,5-dimethyl-4-isoxazolyl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-propyl-1H-indole-5-carbonitrile and 3-(chloromethyl)-5-(3,5-dimethyl-4-isoxazolyl)-1,2,4-oxadiazole 1H NMR (400 MHz, DMSO-d6) δ 7.94 (s, 1 H), 7.75 (d, J=8.5 Hz, 1 H), 7.57 (d, J=8.5 Hz, 1 H), 5.80 (s, 2 H), 2.91 (t, J=4.9 Hz, 2 H), 2.66 (s, 3 H), 2.38 (s, 3 H), 1.71-1.58 (m, 2 H), 0.92 (t, J=7.3 Hz, 3 H); MS (ES) m/z 396 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-30eb684365444cb68eadf2190091ef80
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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