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

HRID 913603Notes

Reaction equation

HRID 913603 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]([CH2:13][CH2:14][CH3:15])[NH:6]2.Br[CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][CH:21]=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]([CH2:13][CH2:14][CH3:15])[N:6]2[CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 6483715N-(4-(2-Bromoethoxy)phenyl)acetamideHCID 674043384-chloro-2-propyl-1H-indole-5-carbonitrile

Product 1

HCID 57800162N-(4-{[2-(4-Chloro-5-cyano-2-propyl-1H-indol-1-yl)ethyl]oxy}phenyl)acetamide

Procedure

Synthesized as described in Example 4 from 4-chloro-2-propyl-1H-indole-5-carbonitrile and N-{4-[(2-bromoethyl)oxy]phenyl}acetamide: 1H NMR (400 MHz, DMSO-d6) δ 9.72 (s, 1 H), 7.90 (s, 1 H), 7.80 (d, J=8.5 Hz, 1 H), 7.54 (d, J=8.5 Hz, 1 H), 7.39 (d, J=9.0 Hz, 2 H), 6.71 (d, J=9.0 Hz, 2 H), 4.63 (t, J=4.9 Hz, 2 H), 4.18 (t, J=4.9 Hz, 2 H), 2.82 (t, J=4.9 Hz, 2 H), 1.94 (s, 3 H), 1.73-1.49 (m, 2 H), 0.94 (t, J=4.9 Hz, 3 H); MS (ES) m/z 396 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-3f9b7beeb4024b4b9f99550d19ef5286
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

Loading…