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

HRID 1398450ノート

反応式

HRID 1398450 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

To a solution of 4-chloro-5-fluoronicotinic acid (1.7 g, 9.68 mmol) in acetonitrile (18 mL) cooled to 0° C. was added DBU (3.65 mL, 24.21 mmol) dropwise. The reaction mixture was stirred for 30 min. To this mixture iodomethane (3.03 mL, 48.4 mmol) was added dropwise and stirred at rt for 12 h. The volatiles were removed under reduced pressure. The residue was purified via silica gel column chromatography (hexane and ethyl acetate) to afford methyl 4-chloro-5-fluoronicotinate (1.2 g, 6.33 mmol, 65% yield) as a yellow solid. LC/MS (ESI) m/e 190.0 [(M+H)+, calcd for C7H6ClFNO2 189.9]; LC/MS retention time (method D): tR=0.77 min.

後処理

  1. stirringstirred at rt for 12 h
  2. customThe volatiles were removed under reduced pressure
  3. customThe residue was purified via silica gel column chromatography (hexane and ethyl acetate)

出典と根拠

ORDレコード
ord-4e9a630db9a94cae8443f414ddd2c21f
出典データセット
uspto-grants-2014_12
特許番号
US08901305B2

反応ノート

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