4-(Chloromethyl)-2-(2-chlorophenyl)-1,3-thiazole → 1-{[2-(2-Chlorophenyl)-1,3-thiazol-4-yl]methyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 1188620Notes

Reaction equation

HRID 1188620 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])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2.Cl[CH2:18][C:19]1[N:20]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[S:22][CH:23]=1>>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[S:22][CH:23]=[C:19]([CH2:18][N:3]2[C:4]3[C:9](=[C:8]([C:11]([F:12])([F:14])[F:13])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])[N:20]=1

Participants

3

Reactant 2

HCID 20635954-(Chloromethyl)-2-(2-chlorophenyl)-1,3-thiazoleHCID 533093462-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 674074731-{[2-(2-Chlorophenyl)-1,3-thiazol-4-yl]methyl}-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 using 2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 120) and 4-(chloromethyl)-2-(2-chlorophenyl)-1,3-thiazole: 1H NMR (400 MHz, CDCl3) δ 8.17 (m, 1H), 7.58 (d, J=8.3 Hz, 1H), 7.49 (m, 2H), 7.36 (m, 2H), 6.79 (s, 1H), 6.65 (s, 1H), 5.51 (s, 2H), 2.58 (s, 3H); MS (ES) m/z 432 (M+1) and 434 (M+1, isotope).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-2d56f858a2044ac0bb7d420170b56d4b
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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