Methanol → Methyl 2-{[1-(tert-butoxycarbonyl)azetidin-3-yl]methyl}-4-methyl-2H-indazol-5-carboxylate
Reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:11][CH:12]3[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]3)[N:7]=2)[C:3]=1[CH3:23].[C:24]([O-:27])(=[O:26])C.[K+].[CH3:29]O>>[C:19]([O:18][C:16]([N:14]1[CH2:15][CH:12]([CH2:11][N:6]2[CH:5]=[C:4]3[C:8]([CH:9]=[CH:10][C:2]([C:24]([O:27][CH3:29])=[O:26])=[C:3]3[CH3:23])=[N:7]2)[CH2:13]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]Participants
4
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 8.16 g of the bromide prepared in Example 117a in 65.4 ml methanol, 6.5 g of 1,1 bis(diphenylphosphino)ferrocen-palladium(II) dichloride and 15 g of potassium acetate were added at 25° C. and the mixture was stirred under CO at 10.15 bar and 120° C. for 24 hours in an autoclave. The reaction mixture was then cooled, filtered through Celite at the pump and the filtrate concentrated in vacuo. The residue thus obtained was purified by chromatography on the Flashmaster (hexane/ethyl acetate 1:0-0:1). 6.97 g of the title compound was obtained.