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

HRID 1259294ノート

反応式

HRID 1259294 の反応式
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

参加物

4

反応物 2

HCID 690582,3-Dimethyl 2,3-pyridinedicarboxylateHCID 178505759HCID 178505759、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-44aaedc0e1204c75928e98200ce08149
出典データセット
uspto-grants-2013_06
特許番号
US08466150B2

反応ノート

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