1-(2-Bromoethoxy)-2,4-difluorobenzene → 4-Chloro-1-{2-[(2,4-difluorophenyl)oxy]ethyl}-2-propyl-1H-indole-5-carbonitrile

HRID 913606Notes

Reaction equation

HRID 913606 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]([F:26])=[CH:22][C:21]=1[F:27]>>[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]([F:26])=[CH:22][C:21]=1[F:27]

Participants

3

Reactant 2

HCID 232942611-(2-Bromoethoxy)-2,4-difluorobenzeneHCID 674043384-chloro-2-propyl-1H-indole-5-carbonitrile

Product 1

HCID 578002244-Chloro-1-{2-[(2,4-difluorophenyl)oxy]ethyl}-2-propyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-propyl-1H-indole-5-carbonitrile and 1-[(2-bromoethyl)oxy]-2,4-difluorobenzene: 1H NMR (400 MHz, DMSO-d6) δ 7.89 (s, 1 H), 7.79 (d, J=8.7 Hz, 1 H), 7.51 (d, J=8.7 Hz, 1 H), 7.25-7.14 (m, 1 H), 7.08-6.99 (m, 1 H), 6.96-6.85 (m, 1 H), 4.67 (t, J=4.9 Hz, 2 H), 4.28 (t, J=4.9 Hz, 2 H), 2.89 (t, J=7.3 Hz, 2 H), 1.73-1.57 (m, 2 H), 0.93 (t, J=7.3 Hz, 3 H); MS (ES) m/z 375 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-b3d6da6dca524bb29a69149b1548c357
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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