Potassium Acetate → HCID 131734389, compound

HRID 1508540Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[B:19]1(B2OCC(C)(C)CO2)[O:24]CC(C)(C)C[O:20]1.C([O-])(=O)C.[K+]>CS(C)=O>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C@H:10]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]2)=[CH:3][C:2]=1[B:19]([OH:24])[OH:20]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl trans-3-(3-iodo-4-methoxyphenyl)cyclopentanecarboxylate (Step C) (64 mg, 0.178 mmol), bis(neopentyl glycolato)diboron (48.2 mg, 0.213 mmol), potassium acetate (100 mg, 1.019 mmol), and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (10 mg, 0.012 mmol) in DMSO (3 ml) was degassed flushing with nitrogen and heated at 80° C. for 1 hour. Then, added ethyl acetate and washed with water followed by brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the titled compound. 1H NMR (500 MHz, CDCl3): δ 7.71 (d, J=2.5 Hz, 1H); 7.29 (m, 1H); 6.85 (m, 1H); 6.10 (s, 2H); 3.90 (s, 3H); 3.70 (s, 3H); 3.19 (m, 1H); 3.02 (m, 1H); 2.35 (ddd, J=13.3, 8.0, 4.6 Hz, 1H); 2.19-2.11 (m, 2H); 2.01-1.85 (m, 2H); 1.72-1.63 (m, 1H).

Workup

customwas degassed
customflushing with nitrogen
additionThen, added ethyl acetate
washwashed with water
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe residue was purified by flash column chromatography on silica gel
washeluting with EtOAc in hexanes

Sources & evidence

ORD record: ord-49784f9280b648839df2ea0fc52e2f8c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221834B2

Reaction notes

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