Triethylamine → 1-[(4-Methoxy)phenyl]-3-(hydroxymethyl)-1H-pyrazole 5-(methoxycarbonyl)pyrazole

HRID 610151Notes

Reaction equation

HRID 610151 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]([C:18]1[NH:22][N:21]=[C:20](C(O)=O)[CH:19]=1)=[O:17].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[N:10]2)=[CH:7][CH:8]=1.[CH3:14][O:15][C:16]([C:18]1[NH:22][N:21]=[CH:20][CH:19]=1)=[O:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 696917091-[(4-methoxy)phenyl]-1H-pyrazole 5-(methoxycarbonyl)pyrazole-3-carboxylic acid

Product 1

HCID 696917971-[(4-Methoxy)phenyl]-3-(hydroxymethyl)-1H-pyrazole 5-(methoxycarbonyl)pyrazoleYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(4-methoxy)phenyl]-1H-pyrazole-5-(methoxycarbonyl)pyrazole-3-carboxylic acid (2.4 g, 8.69 mmol) in 50 mL of tetrahydrofuran at -20° C. was added triethylamine (1.21 mL, 8.69 mmol) and ethyl chloroformate (0.83 mL, 8.69 mmol). This mixture was stirred for 30 min and then there was added sodium borohydride (0.66 g, 17.4 mmol) in a minimal amount of water. The reaction mixture was stirred with slow warming to room temperature for 1 h and then was quenched with 10% aq HCl. After diluting with ethyl acetate, the organics were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (elution with 3:2 ethyl acetate/hexane) to afford 1.4 g (61%) of the title compound. LRMS (DCI): 263.3 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred
  2. customwas quenched with 10% aq HCl
  3. additionAfter diluting with ethyl acetate
  4. washthe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (elution with 3:2 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b82b121abd454bf783847f3710877904
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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