2,3-Dimethyl 2,3-pyridinedicarboxylate → Methyl 2-(2-(4-fluorophenyl)acetyl)nicotinate

HRID 1259294

반응식

HRID 1259294 반응식
CO[C:3]([C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].[F:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][Mg]Cl)=[CH:18][CH:17]=1>O1CCCC1>[F:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][C:3]([C:5]2[N:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[O:4])=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 690582,3-Dimethyl 2,3-pyridinedicarboxylateHCID 178505759HCID 178505759, 화합물

생성물 1

HCID 69046764Methyl 2-(2-(4-fluorophenyl)acetyl)nicotinate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of dimethylpyridine-2,3-dicarboxylate (1.0 g, 5.1 mmol) in tetrahydrofuran (50 ml) was added (4-fluorobenzyl)magnesium chloride (0.25 M in tetrahydrofuran, 20 ml, 5.1 mmol) through a syringe at −78° C. The reaction mixture was stirred at the same temperature for 30 minutes and was quenched with addition of water. After warming up to room temperature, the reaction mixture was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The residue was purified by flash chromatography (15% ethyl acetate in hexane) to give the title compound. MS (DCI/NH3) m/z 274 (M+H)+.

후처리

  1. customwas quenched with addition of water
  2. customthe reaction mixture was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (15% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-44aaedc0e1204c75928e98200ce08149
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466150B2

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