Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[C:25]([O:29][C:30]([NH:32][C:33]1[CH:38]=[C:37](CO)[CH:36]=[CH:35][N:34]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(OCC)(=O)C>C(Cl)Cl>[Br:24][CH2:20][C:37]1[CH:36]=[CH:35][N:34]=[C:33]([NH:32][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH:38]=1Participants
6
Procedure
Triphenylphosphine (970 mg, 3.7 mmol) and carbon tetrabromide (1.5 g, 4.6 mmol) were added to a solution of (2-tert-butoxycarbonylaminopyridin-4-yl)methanol (Reference compound No. 4-1, 690 mg, 3.1 mmol) in methylene chloride (20 mL) under ice-cooling, and the mixture was stirred for 2 hours at room temperature. Ethyl acetate (30 mL) was added to the reaction mixture, the whole was washed with saturated aqueous sodium hydrogen carbonate solution (20 mL) and brine (20 mL), and then dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, and the resulting solid was filtered off with ethyl acetate to give 550 mg of the title reference compound as a colorless solid. (Yield 62%)
Workup
- washthe whole was washed with saturated aqueous sodium hydrogen carbonate solution (20 mL) and brine (20 mL)
- dry with materialdried over anhydrous magnesium sulfate
- customThe organic layer was evaporated under reduced pressure
- filtrationthe resulting solid was filtered off with ethyl acetate
- customto give 550 mg of the title reference compound as a colorless solid
Sources & evidence
- ORD record
- ord-0f5a3073906945fdb8b62484d3049fa9
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07544703B2
Linked notes
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