Butyl Acrylate → butyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate

HRID 1804718노트

반응식

HRID 1804718 반응식
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3].Cl[C:11]1[C:16]([NH2:17])=[CH:15][C:14]([F:18])=[CH:13][N:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCCCC)(=O)C.O>[NH2:17][C:16]1[C:11](/[CH:3]=[CH:2]/[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])=[N:12][CH:13]=[C:14]([F:18])[CH:15]=1

참가 물질

8

반응물 4

HCID 8846Butyl AcrylateHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 447548682-Chloro-5-fluoropyridin-3-amine

생성물 1

HCID 68105236butyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 31272Butyl Acetate용매2회

반응 조건

온도
30 °C

실험 절차

A mixed solution of 150 mL of butyl acetate and 73 mL of butyl acrylate was refluxed with heating for 45 minutes under a nitrogen atmosphere. The reaction mixture was cooled to 30° C., 50.0 g of 2-chloro-5-fluoropyridine-3-amine, 3.8 g of palladium (II) acetate, 44.8 g of triphenylphosphine and 36.6 g of sodium carbonate were added thereto, and the mixture was refluxed for 13 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, 150 mL of water and 700 mL of butyl acetate were added thereto, and the mixture was stirred for 1 hour. Insoluble matter was filtered out, and the filter residue was washed using 50 mL of butyl acetate. The filtrate and the wash liquid were combined, the organic layer was separated, and 800 mL of the solvent was evaporated under reduced pressure. To the obtained residue, 300 mL of cyclohexane and 30 mL of toluene were added dropwise, the mixture was cooled to 5° C., and the solid product was obtained by filtration and washed using a mixed solution of toluene-cyclohexane (1:2) and toluene to give 57.8 g of butyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate as a yellow solid.

후처리

  1. temperaturewith heating for 45 minutes under a nitrogen atmosphere
  2. temperaturethe mixture was refluxed for 13 hours under a nitrogen atmosphere
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationInsoluble matter was filtered out
  5. washthe filter residue was washed
  6. customthe organic layer was separated
  7. custom800 mL of the solvent was evaporated under reduced pressure
  8. additionTo the obtained residue, 300 mL of cyclohexane and 30 mL of toluene were added dropwise
  9. temperaturethe mixture was cooled to 5° C.
  10. customthe solid product was obtained by filtration
  11. washwashed

출처 및 근거

ORD 기록
ord-b92269f88ae54f96a5cc24a4ce4878ce
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354426B2

반응 노트

불러오는 중…