Methanol → Methyl 6-cyanonaphthalene-2-carboxylate
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:47][OH:48].CN([CH:52]=[O:53])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:47][O:48][C:52]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:9]=1)=[O:53]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester from Example 95 (1.50 g, 4.98 mmol) in 20 mL of anhydrous DMF was added palladium(II) acetate (33.53 mg, 0.15 mmol), triphenylphosphine (78.36 mg, 0.30 mmol), triethylamine (1.39 mL, 9.96 mmol) and 5 mL of methanol. This mixture was purged with carbon monoxide for ten minutes. The reaction mixture was then placed under balloon pressure of carbon monoxide and heated to 60° C. for 16 hours. The mixture was then diluted with brine, extracted with EtOAc (3×100 mL), extracts washed with 1N HCl (2×100 mL), dried over MgSO4, and concentrated under reduced pressure. Flash chromatography (hexane to 20% EtOAc/hexane) afforded the desired product as a white solid (525 mg, 50%).
Workup
- customThis mixture was purged with carbon monoxide for ten minutes
- additionThe mixture was then diluted with brine
- extractionextracted with EtOAc (3×100 mL)
- washextracts washed with 1N HCl (2×100 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4b46675ff31b458c9771bf2ace0025cd
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06221914B1
Reaction notes
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