Ethyl Acetate → N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide
Reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16](Cl)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C(OCC)(=O)C>CN(C)C=O>[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH:23]=[CH2:24])[CH:15]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
N-(1-Adamantylmethyl)-2,5-dichloroisonicotinamide (2.32 g) and tributyl(vinyl)stannane (2.61 g) were stirred together in dry N,N-dimethylformamide (50 mL) at room temperature under nitrogen. The latter was treated with a few crystals of 2,6-ditert-butyl-4-methylphenol and dichloro[bis(triphenylphosphine)]palladium(II) (0.24 g). The reaction mixture was warmed to 80° C. for 4 hours and subsequently cooled to room temperature. The mixture was poured into ethyl acetate (50 mL) and washed with water (2×25 mL) then brine (30 mL). The organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20) to afford the sub-titled compound (2.21 g).
Workup
- temperaturesubsequently cooled to room temperature
- washwashed with water (2×25 mL)
- dry with materialThe organics were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20)
Sources & evidence
- ORD record
- ord-51832b83da06471e9b15a13361bcf06a
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129246B2
Reaction notes
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