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

HRID 2186245Notes

Reaction equation

HRID 2186245 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+]>O1CCCC1C([O-])=O.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 21941165TetrahydrofuranatSolvent

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-9e26c6db156b41e68230b26cbc5f7e13
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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