2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile → 1-({5-[3,5-bis(Trifluoromethyl)phenyl]-3-isoxazolyl}methyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 2102153Notes

Reaction equation

HRID 2102153 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[CH:23]=[C:22]([C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=2)[O:21][N:20]=1>>[F:37][C:34]([F:35])([F:36])[C:26]1[CH:25]=[C:24]([C:22]2[O:21][N:20]=[C:19]([CH2:18][N:3]3[C:4]4[C:9](=[C:8]([C:11]([F:12])([F:14])[F:13])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=4)[CH:10]=[C:2]3[CH3:1])[CH:23]=2)[CH:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:27]=1

Participants

3

Reactant 2

HCID 533093462-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrileHCID 578002023-(Chloromethyl)-5-[3,5-bis(trifluoromethyl)phenyl]isoxazole

Product 1

HCID 866207071-({5-[3,5-bis(Trifluoromethyl)phenyl]-3-isoxazolyl}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 3-(chloromethyl)-5-[3,5-bis(trifluoromethyl)phenyl]isoxazole (Example 323C): MS (ES) m/z 518 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-ef95957b3e69413e9099bcb6684d52ae
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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