Trimethyl-(6-methylpyrazin-2-yl)stannane → tert-butyl N-[(3S)-1-[3-cyano-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate
Reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:26])[OH:25])[CH2:18]4)[C:14]([C:27]#[N:28])=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C[Sn](C)(C)[C:31]1[CH:36]=[N:35][CH:34]=[C:33]([CH3:37])[N:32]=1>>[C:27]([C:14]1[C:15]([N:17]2[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:26])[O:25][C:5]([CH3:8])([CH3:6])[CH3:4])[CH2:18]2)=[N:16][C:11]([N:10]2[C:4]3[CH:3]=[C:2]([C:31]4[CH:36]=[N:35][CH:34]=[C:33]([CH3:37])[N:32]=4)[N:7]=[CH:6][C:5]=3[CH:8]=[N:9]2)=[CH:12][CH:13]=1)#[N:28]Participants
3
Reactant 2
Product 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of [(3S)-1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-3-cyano-2-pyridyl]-3-piperidyl]carbamic acid (0.5166 mmol; 205.5 mg), trimethyl-(6-methylpyrazin-2-yl)stannane (0.7749 mmol; 199.1 mg), and palladium(0)tetrakis (triphenylphosphine); (0.05166 mmol; 59.8 mg) in N,N-Dimethylacetamide (12 mL) was purged with Argon. The reaction mixture was sealed in a pressure vial and heated at 150° C. for 2 hours. The mixture was cooled to room temperature, and then partitioned between EtOAc and water. The organic layer was concentrated and the residue was purified on silica eluted with 0 to 5% MeOH in DCM to afford tert-butyl N-[(3S)-1-[3-cyano-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate as a yellow solid (248.6 mg, 94%).