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

HRID 1188418Notes

Reaction equation

HRID 1188418 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][CH:5]=2.Cl[CH2:16][C:17]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[O:19][N:18]=1>>[CH3:1][C:2]1[N:3]([CH2:16][C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=3)[O:19][N:18]=2)[C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]([F:12])([F:14])[F:13])[CH:7]=[CH:6][CH:5]=2

Participants

3

Reactant 2

HCID 27366223-(Chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazoleHCID 196970222-methyl-4-(trifluoromethyl)-1H-indole

Product 1

HCID 578004152-Methyl-4-(trifluoromethyl)-1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-indole

Procedure

Synthesized as described in Example 4 using 2-methyl-4-(trifluoromethyl)-1H-indole and 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole: 1H NMR (400 MHz, CDCl3) δ 8.31 (s, 1H), 8.24 (d, J=8.1 Hz, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.64 (m, 2H), 7.38 (d, J=7.9 Hz, 1H), 7.22 (t, J=7.9 Hz, 1H), 6.52 (s, 1H), 5.45 (s, 2H), 2.66 (s, 3H); MS (ES) m/z 426 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-6d4245d0fc2b43fb90b9efc0a28f4c5f
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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