Bromine → Isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-7-bromo-8-methyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 2353889Notes

Reaction equation

[Br:1]Br.[CH:3]([O:6][C:7]([N:9]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]([C:32](=[O:34])[CH3:33])[CH2:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=2)[C:11]2[CH:35]=[CH:36][C:37]([CH3:39])=[CH:38][C:10]1=2)=[O:8])([CH3:5])[CH3:4]>C(O)(=O)C.C(OCC)(=O)C>[CH:3]([O:6][C:7]([N:9]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]([C:32](=[O:34])[CH3:33])[CH2:17][C:18]2[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[C:20]([C:28]([F:29])([F:30])[F:31])[CH:19]=2)[C:11]2[CH:35]=[C:36]([Br:1])[C:37]([CH3:39])=[CH:38][C:10]1=2)=[O:8])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 50 °C

Procedure

Add bromine (0.016 mL, 0.303 mmol) dropwise to a solution of isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-methyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.153 g, 0.288 mmol) in glacial acetic acid (2.8 mL) and heat at 50° C. under nitrogen for 18 h. Cool the mixture to room temperature, dilute with ethyl acetate (50 mL) and wash with saturated sodium bicarbonate (2×50 mL) and 10% aqueous sodium thiosulfate (50 mL), then dry the organic layer over sodium sulfate, filter and remove the solvent under reduced pressure to provide the title compound as a white solid (0.176 g, >99%): ESI MS 609 (M+H).

Workup

temperatureCool the mixture to room temperature
washwash with saturated sodium bicarbonate (2×50 mL) and 10% aqueous sodium thiosulfate (50 mL)
dry with materialdry the organic layer over sodium sulfate
filtrationfilter
customremove the solvent under reduced pressure

Sources & evidence

ORD record: ord-609f65229e0f4258aacef7aa686b9365
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749992B2

Reaction notes

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