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

HRID 1398450노트

반응식

HRID 1398450 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 86695923Methyl 4-chloro-5-fluoropyridine-3-carboxylate수율 65.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4e9a630db9a94cae8443f414ddd2c21f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901305B2

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