(R)-4-bromo-alpha-methylbenzylamine → HCID 67246165, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16](B(O)O)[CH:17]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([O:21][CH3:22])=[C:14]([C:2]2[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=2)[CH:13]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
A mixture of (R)-1-(4-bromophenyl)ethylamine (0.10 g, 0.5 mmol), 5-fluoro-2-methoxyphenyl boronic acid (0.17 g, 1 mmol), and palladium (II) acetate (0.011 g, 0.05 mmol) was heated for 5 min at 200° C. in a Smithcreator microwave oven. The mixture was then poured onto an SCX column, washed with dichloromethane/methanol, and the intermediate amine eluted using 1M ammonia in methanol (50 ml). Evaporation of solvents under reduced pressure gave (R)-1-(5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine. To a solution of (R)-1-(5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (0.25 g, 0.1 mmol) in dichloromethane (1 ml) was added triethylamine (0.025 g, 0.25 mmol) and 2,4 difluorophenyl-sulfonyl chloride (0.043 g, 0.2 mmol). The solution was stirred overnight and then quenched with acetic acid (0.5 ml). Purification by preparatory LCMS and removal of solvent under reduced pressure gave the title compound: 1H NMR (400 MHz, DMSO): δ 8.58 (d, 1H), 7.64 (q, 1H), 7.30-6.98 (m, 9H), 4.44 (dq, 1H), 3.74 (s, 3H), 1.36 (d, 3H) ppm; MS (ESI) m/z: value [M+H]+.
Workup
- additionThe mixture was then poured onto an SCX column
- washwashed with dichloromethane/methanol
- washthe intermediate amine eluted
- customEvaporation of solvents under reduced pressure
Sources & evidence
- ORD record
- ord-59af4deedc1f4b9a9bbbb619b9660e19
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07960365B2
Reaction notes
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