(3-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate → (6-chloro-3-oxo-1-trityl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate

HRID 588110Notes

Reaction equation

HRID 588110 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]2[C:12]([O:34]CC3C=CC=CC=3)=[N:13][N:14]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[C:8]([Cl:42])[N:7]=1)(=[O:3])[CH3:2]>C(Cl)Cl.CO.[Pd]>[C:1]([O:4][CH2:5][C:6]1[C:11]2[C:12](=[O:34])[NH:13][N:14]([C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[C:8]([Cl:42])[N:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 118271990(3-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate

Product 1

HCID 118272544(6-chloro-3-oxo-1-trityl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (3-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate (2.87 g, 5.00 mmol) in DCM (10 ml) and MeOH (50 ml) was evacuated and backfilled 3× with argon, charged with Pd/C (0.532 g, 0.500 mmol), evacuated and backfilled 3× with H2, then stirred at RT under a balloon of H2 for 1 hr. Filtered through celite, eluted with EtOAc and concentrated filtrate in vacuo to obtain (6-chloro-3-oxo-1-trityl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate. MS: [M+H]+ m/z 484.

Workup

  1. customwas evacuated
  2. customevacuated
  3. filtrationFiltered through celite
  4. washeluted with EtOAc and concentrated filtrate in vacuo

Sources & evidence

ORD record
ord-20ac393d203c43ba8c5d96320098b3fb
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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