1-(4-Bromo-2-fluorophenyl)ethan-1-one → 1-(4-Bromo-2-fluorophenyl)ethan-1-amine

HRID 2422878Notes

Reaction equation

HRID 2422878 reaction equation
C([C:4]1[CH:9]=[C:8]([CH:10]([NH2:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[O:20][CH3:21])C=C.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=O)[CH3:30])=[C:25]([F:32])[CH:24]=1>>[F:32][C:9]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[CH:6]=[CH:7][C:8]=1[CH:10]([NH2:12])[CH3:11].[Br:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([NH2:12])[CH3:30])=[C:25]([F:32])[CH:24]=1

Participants

4

Reactant 2

HCID 219385811-(4-Bromo-2-fluorophenyl)ethan-1-oneHCID 67244664HCID 67244664, compound

Product 2

HCID 185435761-(4-Bromo-2-fluorophenyl)ethan-1-amineHCID 672458741-(3,5'-Difluoro-2'-methoxy-biphenyl-4-yl)-ethylamine

Procedure

1-(3,5′-Difluoro-2′-methoxy-biphenyl-4-yl)-ethylamine was prepared in a similar manner to 1-(2-allyl-5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (Example 34) using 4′-bromo-2′-fluoroacetophenone to give 1-(4-bromo-2-fluoro-phenyl)-ethylamine. To a solution of 1-(3,5′-difluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (20.0 mg, 0.08 mmol) in dichloromethane (1 ml) was added triethylamine (8.1 mg, 0.08 mmol) and 1-methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonyl chloride (14.2 mg, 0.06 mmol). The solution was stirred overnight then the solvent evaporated and the residue purified by flash chromatography over silica gel eluting with dichloromethane. Evaporation of solvent under reduced pressure gave the title compound (20 mg). 1H NMR (400 MHz, CDCl3): δ 7.51 (s, 1H), 7.21-7.16 (m, 2H), 7.14-7.09 (m, 1H), 7.05-6.95 (m, 2H), 6.93-6.88 (m, 1H), 5.11 (d, 1H), 4.76 (dq, 1H), 3.81 (s, 3H), 3.73 (s, 3H), 1.55 (d, 3H) ppm; MS (ESI) m/z: 498.3 [M+Na]+.

Sources & evidence

ORD record
ord-b6eda5b5181c43148547b4c99dc4037e
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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