Methanol → HCID 68527157, compound

HRID 1038147Notes

Reaction equation

HRID 1038147 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[N:8]=[C:7]2[C:32]1[CH:33]=[N:34][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:36]=1)([O-])=O.CO.CCOC(C)=O>[Pd].CCOC(C)=O.CCCCCC>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[N:8]=[C:7]2[C:32]1[CH:33]=[N:34][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:36]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 68530714HCID 68530714, compound

Product 1

HCID 68527157HCID 68527157, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Into a Round bottom flask was added tert-butyl 4-(5-nitro-1-trityl-1H-indazol-3-yl)-1H-pyrazole-1-carboxylate (0.440 g, 0.770 mmol) and 10 mL of MeOH and 5 mL of EtOAc followed by Palladium (0.100 g, 0.000470 mmol). The r×n was degassed under Hydrogen (2000 mL, 90 mmol) in balloon, was stirred overnight. TLC (20% EtOAc/Hexane) and MS showed r×n complete. The r×n was filtered through Celite and was rotovaped to dryness to give tert-butyl 4-(5-amino-1-trityl-1H-indazol-3-yl)-1H-pyrazole-1-carboxylate (0.400 g; Yield=95.9%)

Workup

  1. customThe r×n was degassed under Hydrogen (2000 mL, 90 mmol) in balloon
  2. filtrationThe r×n was filtered through Celite

Sources & evidence

ORD record
ord-cad5f79431de4982bf04dd8c0410d4d7
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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