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

HRID 913611Notes

Reaction equation

HRID 913611 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:13])[NH:6]2.Br[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=1>>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:13])[N:6]2[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 6483715N-(4-(2-Bromoethoxy)phenyl)acetamideHCID 674048784-chloro-2-methyl-1H-indole-5-carbonitrile

Product 1

HCID 57800139N-(4-{[2-(4-Chloro-5-cyano-2-methyl-1H-indol-1-yl)ethyl]oxy}phenyl)acetamide

Procedure

Synthesized as described in Example 4 from 4-chloro-2-methyl-1H-indole-5-carbonitrile and N-{4-[(2-bromoethyl)oxy]phenyl}acetamide: 1H NMR (400 MHz, DMSO-d6) δ 9.72 (s, 1 H), 7.89 (d, J=1.1 Hz, 1 H), 7.77 (d, J=8.5 Hz, 1 H), 7.53 (d, J=8.5 Hz, 1 H), 7.39 (d, J=8.9 Hz, 2 H), 6.73 (d, J=8.9 Hz, 2 H), 4.62 (t, 2 H), 4.19 (t, 2 H), 2.48 (s, 3 H), 1.95 (s, 3H); MS (ES) m/z 368 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-d1cabaaae753443199564ed0f9b32a2c
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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