Water → Methyl 5-benzyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate

HRID 219566노트

반응식

HRID 219566 반응식
C1CCN2C(=NCCC2)CC1.[CH3:12][O:13][C:14](=[O:25])[CH2:15][C:16](=O)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[N:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])=[N+:27]=[N-:28].O>CN(C=O)C>[CH2:17]([C:16]1[N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[N:27]=[N:28][C:15]=1[C:14]([O:13][CH3:12])=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2760261Methyl 3-oxo-4-phenylbutanoateHCID 116079241-Azido-2-fluorobenzene

생성물 1

HCID 68649205Methyl 5-benzyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

DBU (1.33 ml; 8.90 mmol; 1.10 eq.) was dissolved in DMF (17 ml) and put under nitrogen atmosphere. 3-Oxo-4-phenyl-butyric acid methyl ester (Chemcollect, 1.711 g; 8.90 mmol; 1.10 eq.) was added to the mixture and it was stirred for 15 min. Then a solution of 1-azido-2-fluorobenzene, prepared according to Platz, M. S. et al. J. Org. Chem. 1989, 54, 5938-5945, (1.11 g; 8.10 mmol; 1 eq.) in DMF (2 mL) was added dropwise to the solution at room temperature. The mixture was stirred at 90° C. for 2 hours. Water (30 mL) was added to the cooled reaction mixture and the aqueous layer was extracted with EtOAc (3×40 mL). Combined organics were washed with water and brine, dried over MgSO4 and concentrated under vacuum giving the title compound as a yellow oil. It was used in the next step without further purification. LC/MS (Method B): 312.1 (M+H)+.

후처리

  1. stirringThe mixture was stirred at 90° C. for 2 hours
  2. extractionthe aqueous layer was extracted with EtOAc (3×40 mL)
  3. washCombined organics were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-ada29ddcb8794e7bba0aa8532d0d35de
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202856B2

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