N-(4-(2-Bromoethoxy)phenyl)acetamide → N-[4-({2-[5-Cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]ethyl}oxy)phenyl]acetamide

HRID 1188444Notes

Reaction equation

HRID 1188444 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.Br[CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=1>>[C:15]([C:7]1[C:8]([C:11]([F:12])([F:14])[F:13])=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]([CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=1)[C:2]([CH3:1])=[CH:10]2)#[N:16]

Participants

3

Reactant 2

HCID 6483715N-(4-(2-Bromoethoxy)phenyl)acetamideHCID 533093462-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 67404875N-[4-({2-[5-Cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]ethyl}oxy)phenyl]acetamide

Procedure

Synthesized as described in Example 4 using 2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile and N-{4-[(2-bromoethyl)oxy]phenyl}acetamide: 1H NMR (400 MHz, DMSO-d6) δ 9.72 (s, 1H), 8.00 (d, J=8.6 Hz, 1H), 7.69 (d, J=8.6 Hz, 1H), 7.39 (d, J=9.0 Hz, 2H), 6.72 (d, J=9.0 Hz, 2H), 6.55 (s, 1H), 4.65 (t, J=5.0 Hz, 2H), 4.21 (t, J=5.0 Hz, 2H), 2.55 (s, 3H), 1.95 (s, 3H); MS (ES) m/z 402 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-1cdf95453df54f7eb6103983f21174ee
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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