Water → HCID 14495336, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=1.O.[CH3:22][N:23](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([C:22]#[N:23])[CH:5]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
4-Cyano-3-(trifluoromethanesulfonyloxy)-benzoic acid methyl ester (from L-819,063 step 1, 4.92 g, 16 mmol) was dissolved in DMF (22.9 ml) and treated with Zn(CN)2 (1.3 g, 11.2 mmol). The reaction mixture was degassed by bubbling in argon for 1 hr. Pd(PPh3)4 (924 mg, 0.8 mmol) was then added and the reaction was heated to 100° C. for 15 hours. The reaction mixture was poured into water (20 mL) and extracted with EtOAc (2×20 mL). The organic layer was washed with water (2×10 mL), 5% HCl (1×10 mL), brine (1×10 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (100% CH2Cl2) to yield the desired compound. FAB MS: 187 m/z (M+ +H)
Workup
- customThe reaction mixture was degassed
- customby bubbling in argon for 1 hr
- extractionextracted with EtOAc (2×20 mL)
- washThe organic layer was washed with water (2×10 mL), 5% HCl (1×10 mL), brine (1×10 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (100% CH2Cl2)
Sources & evidence
- ORD record
- ord-5694c19e02a046e5a410a22d866e60b6
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05939439
Reaction notes
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