Water → 6-({[t-Butyl(dimethyl)silyl]oxy}methyl)nicotinonitrile
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[N:6][CH:7]=1.O.[CH3:18][N:19]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Si:10]([O:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([C:18]#[N:19])=[CH:7][N:6]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A solution of 5-bromo-2-({[t-butyl(dimethyl)silyl]oxy}methyl)pyridine (0.30 g, 1.0 mmol) that was obtained in Example 23 (23a), zinc cyanide (0.18 g, 1.5 mmol), bis(dibenzylideneacetone)palladium (18 mg, 0.02 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (44 mg, 0.08 mmol) in N-methyl-2-pyrrolidinone (4 ml) was stirred at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into water and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:9) as the eluent to afford the title compound (0.23 g) in a yield of 93% as a white crystalline solid.
Workup
- temperatureAfter cooling to room temperature
- extractionextracted with ether
- washThe extract was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over magnesium sulfate
- filtrationAfter filtration
- customthe filtrate was evaporated in vacuo
Sources & evidence
- ORD record
- ord-c563039b8dfd485a8dac4f4967d7e6a6
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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