Ammonia → 3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

HRID 1874784Notes

Reaction equation

HRID 1874784 reaction equation
Br[CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[NH3:21]>C(Cl)Cl.CO>[NH2:21][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 594515763-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (1.0 g, 2.6 mmol) was dissolved in CH2Cl2 (5 mL) and added dropwise to ammonia in methanol (7N, 25 mL). The reaction mixture was stirred for 2 h then the solvent was evaporated. The resulting oil was purified by column chromatography (CH-2Cl2/MeOH) to afford the title compound (0.7 g, 84%). 1H NMR (400 MHz, DMSO-d6): δ ppm 7.79 (s, 2H), 7.45-7.56 (m, 4H), 7.42 (t, 1H), 3.75 (s, 2H). MS: m/z 311.1 (M+1).

Workup

  1. customthe solvent was evaporated
  2. customThe resulting oil was purified by column chromatography (CH-2Cl2/MeOH)

Sources & evidence

ORD record
ord-3fe234e267e74dd58bcdb372fad578a4
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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