Potassium Phosphate, Tribasic → HCID 66905461, compound

HRID 1689734Notes

Reaction equation

[O-]P([O-])([O-])=O.[K+].[K+].[K+].[N:9]1([C:14]([C:16]2[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=2)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:25]([O:27][C:28]([C:30]1=[CH:31][C:32]2[CH:47]=[CH:46][C:45](Br)=[CH:44][C:33]=2[N:34]=[C:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:36]1)=[O:29])[CH3:26]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C>[CH2:25]([O:27][C:28]([C:30]1=[CH:31][C:32]2[CH:47]=[CH:46][C:45]([C:19]3[CH:20]=[CH:21][C:16]([C:14]([N:9]4[CH2:13][CH2:12][CH2:11][CH2:10]4)=[O:15])=[CH:17][CH:18]=3)=[CH:44][C:33]=2[N:34]=[C:35]([C:37]([O:39][C:40]([CH3:43])([CH3:41])[CH3:42])=[O:38])[CH2:36]1)=[O:29])[CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

Preparation of (1E,4E)-ethyl-2-(tert-butoxycarbonyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxylate(23): To an ethanol solution (15 mL) containing K3PO4 (938 mg, 4.42 mmol), 4-(pyrrolidine-1-carbonyl)phenylboronic acid (785 mg, 3.58 mmol), and (1E,4E)-ethyl-8-bromo-2-(tert-butoxycarbonyl)-3H-benzo[b]azepine-4-carboxylate (489 mg, 1.19 mmol), was added palladium acetate (80.5 mg, 0.358 mmol). The reaction was heated to 60° C. for 2 hours, then cooled to room temperature and concentrated to dryness. The brown oil was purified by preparative LC plate (100% EtOAc) to provide (1E,4E)-ethyl-2-(tert-butoxycarbonyl)-8(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxylate (277 mg, 46% yield) as a tan oil.

Workup

temperaturecooled to room temperature
concentrationconcentrated to dryness
customThe brown oil was purified by preparative LC plate (100% EtOAc)

Sources & evidence

ORD record: ord-34c9646ad60e4e1b8d385f552835e271
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153622B2

Reaction notes

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