1,1'-Carbonyldiimidazole → 3-Fluoro-N-methoxy-N-methylpicolinamide

HRID 573348ノート

反応式

HRID 573348 の反応式
[F:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:24][NH:25][O:26][CH3:27].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[C:3]([C:8]([N:25]([O:26][CH3:27])[CH3:24])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27627863-Fluoropyridine-2-carboxylic acid

生成物 1

HCID 866889893-Fluoro-N-methoxy-N-methylpicolinamide収率 94.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 3-fluoropicolinic acid (17.7 g) in THF (300 mL) was added CDI (22.4 g) at room temperature, and the mixture was stirred at room temperature for 30 min and heated to 50° C. After stirring at 50° C. for 1 h, the mixture was cooled to room temperature. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (18.4 g) and DIPEA (32.9 mL) at room temperature, and the mixture was stirred at room temperature for 12 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt) to give the title compound (21.8 g).

後処理

  1. temperatureheated to 50° C
  2. stirringAfter stirring at 50° C. for 1 h
  3. temperaturethe mixture was cooled to room temperature
  4. stirringthe mixture was stirred at room temperature for 12 h
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt)

出典と根拠

ORDレコード
ord-2b5f36724e144136bb7fb640ab418644
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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