Cesium fluoride → Methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate

HRID 533398노트

반응식

HRID 533398 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[Cl:16].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1OB(O)O.[F-].[Cs+].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[Cl:16][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[C:21]1[CH:20]=[CH:19][C:18]([F:17])=[CH:23][C:22]=1[F:24])=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=2

참가 물질

7

반응물 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 222378292,4-Difluorophenylboric acidHCID 67773454Methyl 4-bromo-3-chloroquinoline-6-carboxylate

생성물 1

HCID 67773515Methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate수율 69.3%

시약·촉매·용매 2

HCID 178506421HCID 178506421, 화합물촉매HCID 962Water용매2회

반응 조건

온도
100 °C

실험 절차

Under argon gas atmosphere, a mixture of methyl 4-bromo-3-chloroquinoline-6-carboxylate (130 mg), 2,4-difluorophenylboric acid (137 mg), a 1,1′-bis(diphenylphosphino)ferrocene palladium (H) dichloride/dichloromethane complex (177 mg), cesium fluoride (197 mg), 1,4-dioxane (8 mL), and water (2 mL) was heated under stirring in an oil bath at 100° C. for one day. The reaction mixture was returned to room temperature, and water was added, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate (100 mg).

후처리

  1. customwas returned to room temperature
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-777a251daad84671af204320cfc450bb
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853242B2

반응 노트

불러오는 중…