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

HRID 2101982Notes

Reaction equation

HRID 2101982 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]3[C:11]([CH:12]=2)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=3)[CH2:3][CH2:2]1.Cl[CH2:20][C:21]1[N:25]=[C:24]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=2)[O:23][N:22]=1>>[CH:1]1([C:4]2[N:5]([CH2:20][C:21]3[N:25]=[C:24]([C:26]4[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=4)[O:23][N:22]=3)[C:6]3[C:11]([CH:12]=2)=[C:10]([C:13]([F:14])([F:15])[F:16])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=3)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 431202093-(Chloromethyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazoleHCID 674044722-cyclopropyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 674063572-Cyclopropyl-1-{[5-(3,5-difluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 using 2-cyclopropyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile and 3-(chloromethyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazole: 1H NMR (400 MHz, CDCl3) δ 7.67 (d, J=8.5 Hz, 1H), 7.57 (m, 3H), 7.05 (t, J=8.5 Hz, 1H), 6.48 (s, 1H), 5.64 (s, 2H), 2.13 (m, 1H), 1.15 (m, 2H), 0.92 (m, 2H); MS (ES) m/z 445 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-bf02e6629131442bbce1e47d62abd91b
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

Loading…