Methanol → HCID 54000692, compound
Reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(P(C1C=CC=CC=1)C1C=CC=CC=1)CCP(C1C=CC=CC=1)C1C=CC=CC=1.CN([CH:43]=[O:44])C.[CH3:45][OH:46]>C(OCC)C.C(OCC)(=O)C.C(N(CC)CC)C>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([C:45]([O:44][CH3:43])=[O:46])=[N:7][CH:6]=1)(=[O:10])[CH3:9]Participants
Conditions
- Temperature
- 70 °C
Procedure
1-(6-Bromopyridin-3-yl)ethanone (5.00 g), propane-1,3-diylbis(diphenyl phosphine) (1.546 g), DMF (55 mL), methanol (30 mL), and triethylamine (10.5 mL) were mixed, and the inside of the reaction vessel was degassed and replaced with argon. Palladium acetate (II) (842 mg) was added thereto, and then the inside of the reaction vessel was replaced with carbon monoxide and stirred at 70° C. for 2 days. After leaving to be cooled to room temperature, the reaction mixture was diluted with a mixed liquid of diethyl ether-ethyl acetate, and washed with water and saturated brine in this order. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 5-acetylpyridine-2-carboxylate (1.16 g).
Workup
- customthe inside of the reaction vessel was degassed
- additionPalladium acetate (II) (842 mg) was added
- customAfter leaving
- temperatureto be cooled to room temperature
- washwashed with water and saturated brine in this order
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-26cee0cfaf114b91a585b52607bac561
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598355B2
Reaction notes
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