Methyl iodide → Methyl 4-chloro-5-fluoropyridine-3-carboxylate

HRID 870930ノート

反応式

HRID 870930 の反応式
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:11].[CH2:12]1CCN2C(=NCCC2)CC1.IC>C(#N)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:12])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:11]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 114579884-chloro-5-fluoropyridine-3-carboxylic acid

生成物 1

HCID 86695923Methyl 4-chloro-5-fluoropyridine-3-carboxylate収率 65.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 4-chloro-5-fluoronicotinic acid (1.7 g, 9.68 mmol) in acetonitrile (18 mL) was cooled to 0° C. To this solution was added DBU (3.65 mL, 24.21 mmol) dropwise and the resultant solution stirred for 30 min. Iodomethane (3.03 mL, 48.4 mmol) was added dropwise and stirred at room temperature for 12 h. The volatiles were removed completely under reduced pressure and the residue purified via silica gel chromatography using a gradient of ethyl acetate in hexane to afford methyl 4-chloro-5-fluoronicotinate (1.2 g, 6.33 mmol, 65% yield) as a yellow solid. LCMS (ESI) m/e 190.0 [(M+H)+, calcd for C7H6ClFNO2 190.0]; LC/MS retention time (Method F): tR=0.77 min.

後処理

  1. customThe volatiles were removed completely under reduced pressure
  2. customthe residue purified via silica gel chromatography

出典と根拠

ORDレコード
ord-39655b3d7939410fab37072801e8711a
出典データセット
uspto-grants-2015_03
特許番号
US08969564B2

反応ノート

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