Hydrogen Bromide → (-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

HRID 1668357Notes

Reaction equation

Br.[Br:2][C:3]1[C:27]([F:28])=[CH:26][C:6]2[O:7][C:8]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:9]=3[C@H:10]3[C@H:15]([NH:16]C(=O)OC)[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1.[OH-].[Na+]>C(O)(=O)C>[Br:2][C:3]1[C:27]([F:28])=[CH:26][C:6]2[O:7][C:8]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:9]=3[C@H:10]3[C@H:15]([NH2:16])[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of acetic acid (80 mL) and hydrogen bromide (48%, 40 mL) was added to methyl (±)-(cis)-(7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate (38.2 mmol), and the mixture stirred overnight at 100° C. After cooling down the reaction mixture was poured into a cold 1N NaOH solution (pH 9). It was extracted with ethyl acetate and the organic layer was washed with brine, dried (Na2SO4) and the solvent was evaporated under reduced pressure to yield the crude title compound (12.7 g, 87%) which was used without further purification. (m/z)=381+383 (M+H)+.

Workup

temperatureAfter cooling down the reaction mixture
extractionIt was extracted with ethyl acetate
washthe organic layer was washed with brine
dry with materialdried (Na2SO4)
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-19cefacc63994b60876e97209bb19297
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989442B2

Reaction notes

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