Ammonia → HCID 68722394, compound

HRID 1875211Notes

Reaction equation

HRID 1875211 reaction equation
[NH3:1].[Br:2][CH2:3][C:4]1[C:5]([F:21])=[C:6]([O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[F:20])[C:7]([Cl:10])=[CH:8][CH:9]=1>C(Cl)Cl>[BrH:2].[NH2:1][CH2:3][C:4]1[C:5]([F:21])=[C:6]([O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[F:20])[C:7]([Cl:10])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 687226214-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile

Product 1

HCID 68722394HCID 68722394, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ammonia (7.0 N solution in MeOH) (47.5 ml, 332 mmol) was added dropwise 4-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile (1.49 g, 4.16 mmol) in solution of 20 mL DCM. The mixture was stirred overnight and the solvent was removed to give 4-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile hydrobromide (1.26 g, 3.35 mmol, 81% yield). 1H NMR (400 MHz, DMSO-d6) d ppm 8.10 (dd, 1H), 7.66 (d, 1H), 7.57-7.63 (m, 1H), 7.54 (t, 1H), 7.02 (br. s., 2H), 6.93 (t, 1H), 4.00 (s, 2H). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.10 (dd, 1H), 7.66 (d, 1H), 7.57-7.63 (m, 1H), 7.54 (t, 1H), 7.02 (br. s., 2H), 6.93 (t, 1H), 4.00 (s, 2H).

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-778a9c0c28ba40a586fce5b3318de1e5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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