Pyrazole → Ethyl 4-((1H-pyrazol-1-yl)methyl)-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate

HRID 2388230Notes

Reaction equation

HRID 2388230 reaction equation
Br[CH2:2][C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([O:20]C(=O)C(C)(C)C)=[C:5]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:4]=1.[NH:32]1[CH:36]=[CH:35][CH:34]=[N:33]1.C1(C)C=CC=CC=1>CCOC(C)=O>[N:32]1([CH2:2][C:3]2[C:8]3[C:9]([C:12]4[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=4)=[N:10][O:11][C:7]=3[C:6]([OH:20])=[C:5]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:4]=2)[CH:36]=[CH:35][CH:34]=[N:33]1

Participants

5

Reactant 3

HCID 1048Pyrazole2×HCID 1140TolueneHCID 67529608Ethyl 4-(bromomethyl)-3-(4-methoxyphenyl)-7-(pivaloyloxy)isoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 67529978Ethyl 4-((1H-pyrazol-1-yl)methyl)-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylateYield 69.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-(bromomethyl)-3-(4-methoxyphenyl)-7-(pivaloyloxy)isoxazolo[4,5-c]pyridine-6-carboxylate (34 mg, 0.069 mmol) and pyrazole (9.4 mg, 0.138 mmol) were added to 1 mL of toluene, and the mixture was stirred at room temperature for 48 h. An additional equiv. of pyrazole was added, and the mixture was stirred at room temperature for 16 h and then at 45° C. for 16 h. The mixture was diluted with EtOAc (20 mL) and washed with 1M hydrochloric acid. The organic layer was dried over MgSO4 and concentrated, and the residue was purified by flash chromatography (0-100% EtOAc/hexanes) to give 19 mg of the title compound. MS: (+) m/z 395.29 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. waitat 45° C. for 16 h
  3. washwashed with 1M hydrochloric acid
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c72b2a0d0032460f968aa1f341c7b12f
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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