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

HRID 913600Notes

Reaction equation

HRID 913600 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[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=2)[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[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=2)[O:18][N:17]=1

Participants

3

Reactant 2

HCID 431202093-(Chloromethyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazoleHCID 674048784-chloro-2-methyl-1H-indole-5-carbonitrile

Product 1

HCID 578001174-Chloro-1-{[5-(3,5-difluorophenyl)-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-difluorophenyl)-1,2,4-oxadiazole: 1H NMR (400 MHz, DMSO-d6) δ 7.94 (d, J=1.1 Hz, 1 H), 7.81 (d, J=8.7 Hz, 1 H), 7.75-7.71 (m, 2 H), 7.69-7.63 (m, 1 H), 7.58 (dd, J=8.7, 1.5 Hz, 1 H), 5.83 (s, 2 H), 2.47 (s, 3 H); MS (ES) m/z 385 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-99bf9ba265334220842be706764444fe
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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