3-Nitrophenylboronic Acid → 3-Hydroxy-5-(3'-nitro-biphenyl-4-yl)-pentanoic acid

HRID 1297251Notes

Reaction equation

[OH:1][CH:2]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)[CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[N+:22]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)([O-:24])=[O:23]>CN(C)C=O.[Pd]>[OH:1][CH:2]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:22]([O-:24])=[O:23])[CH:30]=2)=[CH:11][CH:10]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

3-Hydroxy-5-(4iodo-phenyl)-pentanoic acid (Intermediate 10, 16 mg, 50 μmol), cesium carbonate (40 mg, 125 μmol), 3-nitrophenylboronic acid (10 mg, 60 μmol) and FibreCat™ 1001 (20 mg, 2.7% w/w palladium) were suspended in dimethylformamide (200 μL) and then heated at 100° C. for 1 hour. The reaction was cooled to room temperature and the solvent removed under reduced pressure. The residue was partitioned between 10% methanol/dichloromethane and 2 M HCl then the phases separated. The organic phase was evaporated under reduced pressure and the residue purified via mass directed HPLC to give the title compound (5 mg, 32%) as a white solid. LC/MS: 3.18 min; z/e 314, calcd (M−1) 314. 1H NMR (400 MHz: DMSO-d6): 8.4 (1 H), 8.15 (2 H), 7.7 (3 H), 7.35 (2 H), 3.85 (1 H), 2.7 (2 H), 2.32 (2 H), 1.7 (2 H).

Workup

temperatureThe reaction was cooled to room temperature
customthe solvent removed under reduced pressure
customThe residue was partitioned between 10% methanol/dichloromethane and 2 M HCl
customthe phases separated
customThe organic phase was evaporated under reduced pressure
customthe residue purified via mass

Sources & evidence

ORD record: ord-d6e1944947524f2c99e85539a554887d
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250439B2

Reaction notes

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