Borane;tetrahydrofuran → [(3-Bromo-4-fluorophenyl)methyl](methyl)amine

HRID 657366Notes

Reaction equation

C[C:2]([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Br:17])[CH:11]=1)C(=O)[O-])(C)C.B.C1COCC1>C1COCC1>[Br:17][C:12]1[CH:11]=[C:10]([CH2:9][NH:5][CH3:2])[CH:15]=[CH:14][C:13]=1[F:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of 1,1-dimethylethyl[(3-bromo-4-fluorophenyl)methyl]carbamate (0.755 g, 2.48 mmol) in THF (1 mL) was added BH3.THF (12.5 mL, 1.0 M in THF). The mixture was heated in a microwave machine at about 80° C. for about 30 mins twice. The reaction was then quenched with HCl (10 mL, 1 N) slowly, stirred for 2 h at room temperature, basified with NaHCO3 to pH ˜9, and extracted with EtOAc (50+20 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated to afford 0.52 g (96%) of the title compound. LC-MS m/z 218 (M+H)+.

Workup

customThe reaction was then quenched with HCl (10 mL, 1 N) slowly
extractionextracted with EtOAc (50+20 mL)
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a6df705ab80d4a47923871b64a16cd65
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071588B2

Reaction notes

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