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

HRID 913547Notes

Reaction equation

HRID 913547 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.[F:19][C:20]([F:35])([F:34])[C:21]1[CH:22]=[C:23]([C:27]2[O:31][N:30]=[C:29]([CH2:32]Cl)[N:28]=2)[CH:24]=[CH:25][CH:26]=1>>[CH:1]1([C:4]2[N:5]([CH2:32][C:29]3[N:28]=[C:27]([C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:35])([F:19])[F:34])[CH:22]=4)[O:31][N:30]=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 27366223-(Chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazoleHCID 674044722-cyclopropyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 866206762-Cyclopropyl-4-(trifluoromethyl)-1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 using 2-cyclopropyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile and 5-[3-(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazole: 1H NMR (400 MHz, CDCl3) δ 8.32 (s, 1H), 8.24 (d, J=7.8 Hz, 1H), 7.85 (d, J=7.8 Hz, 1H), 7.66 (m, 2H), 7.55 (d, J=8.5 Hz, 1H), 6.49 (d, J=2.0 Hz, 1H), 5.65 (s, 2H), 2.15 (m, 1H), 1.16 (m, 2H), 0.91 (m, 2H); MS (ES) m/z 477 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-bb43524044154edbadbbb302b33c03f9
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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