Ethanol → trans-2-(4'-Amino-biphenyl-4-carbonyl)-cyclopentanecarboxylic acid

HRID 557715Notes

Reaction equation

Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:28]=[CH:27][C:16]([C:17]([C@@H:19]2[CH2:23][CH2:22][CH2:21][C@H:20]2[C:24]([OH:26])=[O:25])=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([C@@H:19]3[CH2:23][CH2:22][CH2:21][C@H:20]3[C:24]([OH:26])=[O:25])=[O:18])=[CH:27][CH:28]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 4-aminophenylboronic acid hydrochloride (0.21 g, 1.2 mmol), trans-2-(4-bromo-benzoyl)-cyclopentanecarboxylic acid (0.30 g, 1 mmol), tetrakis(triphenylphosphine) palladium (0) (10 mg), 2 M aqueous sodium carbonate solution (0.5 mL), ethanol (2 mL), and ethylene glycol dimethyl ether (3 mL) was heated under microwave condition to 160° C. for 30 min. The crude reaction mixture was adsorbed onto silica gel and flash chromatography (eluting with ethyl acetate and hexanes) yielded 0.2 g of trans-2-(4′-amino-biphenyl-4-carbonyl)-cyclopentanecarboxylic acid as a brown solid. LCMS calcd for C19H19NO3 (m/e) 309, obsd 310 (M+H).

Workup

customThe crude reaction mixture
washwas adsorbed onto silica gel and flash chromatography (eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record: ord-1b18b7f26f0b465eb1f84ce1cd3e7b85
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058299B2

Reaction notes

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