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

HRID 913609Notes

Reaction equation

HRID 913609 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]([F:24])=[CH:20][C:19]=1[F:25]>>[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]([F:24])=[CH:20][C:19]=1[F:25]

Participants

3

Reactant 2

HCID 232942611-(2-Bromoethoxy)-2,4-difluorobenzeneHCID 674048784-chloro-2-methyl-1H-indole-5-carbonitrile

Product 1

HCID 578004284-Chloro-1-{2-[(2,4-difluorophenyl)oxy]ethyl}-2-methyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-methyl-1H-indole-5-carbonitrile and 1-[(2-bromoethyl)oxy]-2,4-difluorobenzene: 1H NMR (400 MHz, DMSO-d6) δ 7.88 (s, 1 H), 7.76 (d, J=8.7 Hz, 1 H), 7.50 (d, J=8.7 Hz, 1 H), 7.26-7.15 (m, 1 H), 7.10-7.00 (m, 1 H), 6.92-6.88 (m, 1 H), 4.67 (t, J=5.0 Hz, 2 H), 4.30 (t, J=5.0 Hz, 2 H), 3.30 (s, 3 H); MS (ES) m/z 347 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-320da06382564159a19d389edb0f35dc
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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