N-methyl-2-pyrrolidone → HCID 71272391, compound
Reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.[CH3:17][N:18]1C(=O)CCC1>[C-]#N.[C-]#N.[Zn+2]>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:2]([C:17]#[N:18])[C:3]=2[CH:4]=[N:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To a mixture of 196 (0.57 g, 2.05 mmol), Zn(CN)2 (264 mg, 2.25 mmol) in NMP (6 mL) under an argon atmosphere was added (Ph3P)4Pd(0) (356 mg, 0.31 mmol). The mixture was heated at 85° C. overnight, cooled, and partitioned between EtOAc (300 mL) and H2O (50 mL). The organic layer was separated and washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with 1% MeOH/DCM to afford 430 mg (75%) of 1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (198) as yellow solid: MS (ESI) m/z=228 [M+1]+.