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

HRID 1875083Notes

Reaction equation

HRID 1875083 reaction equation
CP(C)C.O.[N:6]([CH2:9][C:10]1[C:11]([F:27])=[C:12]([O:17][C:18]2[CH:19]=[C:20]([CH:23]=[C:24]([Cl:26])[CH:25]=2)[C:21]#[N:22])[C:13]([Br:16])=[CH:14][CH:15]=1)=[N+]=[N-]>C1COCC1>[NH2:6][CH2:9][C:10]1[C:11]([F:27])=[C:12]([O:17][C:18]2[CH:19]=[C:20]([CH:23]=[C:24]([Cl:26])[CH:25]=2)[C:21]#[N:22])[C:13]([Br:16])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 866449253-{[3-(Azidomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethylphosphine (1M in THF) (6.41 mL, 6.41 mmol) and water (0.384 mL, 21.36 mmol) were added to a solution of 3-{[3-(azidomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (1.630 g, 4.27 mmol) in THF (30 mL) at RT. The mixture was stirred at RT overnight. The solvent was evaporated. The residue was purified by chromatography with dichloromethane:methanol to give the title compound (1.21 g, 79%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.80 (s, 1H), 7.60 (dd, 1H), 7.43-7.51 (m, 2H), 7.41 (t, 1H), 3.75 (s, 2H), 1.92 (br. s., 2H).

Workup

  1. customThe solvent was evaporated
  2. customThe residue was purified by chromatography with dichloromethane

Sources & evidence

ORD record
ord-c7696ed23204489f924a207964845ad2
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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