Methanol → Methyl 2-{[1-(tert-butoxycarbonyl)azetidin-3-yl]methyl}-4-methyl-2H-indazol-5-carboxylate

HRID 2174928Notes

Reaction equation

HRID 2174928 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

Reactant 3

HCID 887MethanolHCID 517044Potassium AcetateHCID 117690535Tert-butyl 3-[(5-bromo-4-methyl-2H-indazol-2-yl)methyl]-azetidin-1-carboxylate

Product 1

HCID 89601734Methyl 2-{[1-(tert-butoxycarbonyl)azetidin-3-yl]methyl}-4-methyl-2H-indazol-5-carboxylate

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.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationfiltered through Celite at the pump
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue thus obtained
  5. customwas purified by chromatography on the Flashmaster (hexane/ethyl acetate 1:0-0:1)

Sources & evidence

ORD record
ord-7056892e87394c0cb09c58a819042d71
Source dataset
uspto-grants-2015_06
Patent number
US09062041B2

Reaction notes

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