Ethanol → ethyl 5-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-3-fluoropyridine-2-carboxylate

HRID 1026219Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[CH:4][C:3]=1[F:20].C(N(CC)CC)C.[CH2:28]([OH:30])[CH3:29].CN([CH:34]=[O:35])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[C:15]([O:14][C:13]([NH:12][C@@H:10]([CH3:11])[CH2:9][O:8][C:5]1[CH:4]=[C:3]([F:20])[C:2]([C:34]([O:30][CH2:28][CH3:29])=[O:35])=[N:7][CH:6]=1)=[O:19])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

Under a carbon monoxide atmosphere, a mixture of tert-butyl {(1S)-2-[(6-chloro-5-fluoropyridin-3-yl)oxy]-1-methylethyl}carbamate (500 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (135 mg), triethylamine (0.229 mL), ethanol (5 mL) and DMF (5 mL) was stirred at 80° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (402 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe combined organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-10c0a04ef7084f16998ced29b0ee4f0e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729102B2

Reaction notes

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