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

HRID 610151노트

반응식

HRID 610151 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b82b121abd454bf783847f3710877904
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998424

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