Borane;tetrahydrofuran → HCID 68109324, compound

HRID 2179359Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](=O)[NH:10][CH2:11][CH2:12][CH2:13][C:14]=3[O:15][C:4]=2[CH:3]=1.B.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:9][NH:10][CH2:11][CH2:12][CH2:13][C:14]=3[O:15][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a slurry of the product of step C (858 mg, 3.06 mmol) in anhydrous THF (6 mL) was added 1 M borane-THF complex (1 N in THF, 15.3 mL, 15.3 mmol) at ambient temperature. The reaction mixture was heated to 65° C. for 15 h. After cooling to ambient temperature, the reaction mixture was quenched with 1 M HCl and concentrated in vacuo. The residue was basified with 1 M NaOH and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude material which was purified by flash column chromatography (SiO2, 90:10 dichloromethane/methanol) to provide 8-bromo-2,3,4,5-tetrahydro-1H-benzofuro[3,2-c]azepine (369 mg, 45%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.53 (d, J=1.8 Hz, 1H), 7.33-7.28 (m, 1H), 7.21 (d, J=8.4 Hz, 1H), 3.95 (s, 2H), 3.18 (td, J=3.9, 2.4 Hz, 2H), 3.00 (t, J=6.0 Hz, 2H), 1.94-1.84 (m, 2H), 1.57 (s, 1H).

Workup

temperatureAfter cooling to ambient temperature
customthe reaction mixture was quenched with 1 M HCl
concentrationconcentrated in vacuo
extractionextracted with dichloromethane
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give the crude material which
customwas purified by flash column chromatography (SiO2, 90:10 dichloromethane/methanol)

Sources & evidence

ORD record: ord-cf07bfbebc5c43eea42a66ee723cbf46
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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