Ammonia → HCID 86644947, compound

HRID 1875178Notes

Reaction equation

HRID 1875178 reaction equation
[NH3:1].[Br:2][C:3]1[C:4]([Cl:22])=[C:5]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=2)[C:16]#[N:17])[C:6]([F:11])=[C:7]([CH2:9]Br)[CH:8]=1>C(Cl)Cl>[NH2:1][CH2:9][C:7]1[C:6]([F:11])=[C:5]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=2)[C:16]#[N:17])[C:4]([Cl:22])=[C:3]([Br:2])[CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86644945HCID 86644945, compound

Product 1

HCID 86644947HCID 86644947, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ammonia (7.0 M solution in MeOH) (60.0 ml, 2771 mmol) solution was added 3-{[3-bromo-5-(bromomethyl)-2-chloro-6-fluorophenyl]oxy}-5-chlorobenzonitrile in DCM (40 ml) dropwise at 0° C. and the reaction mixture was allowed to warm to rt overnight. The solvent was removed, the residue dissolved in EtOAc and the mixture was neutralized with saturated sodium bicarbonate. The solvent was removed and the crude material was purified via silica gel chromatography to give the title compound 3-{[3-(aminomethyl)-5-bromo-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (801 mg, 2.054 mmol, 95% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.88 (d, 1H), 7.77 (s, 1H), 7.25-7.60 (m, 2H), 3.72 (s, 2H), 1.98 (br. s., 2H)

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in EtOAc
  3. customThe solvent was removed
  4. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-94a28c5e8adf4683bd03835b1a423e84
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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