Cesium carbonate → 7-bromo-1-fluoro-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one

HRID 455699노트

반응식

HRID 455699 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[N:13]=[C:12]([F:22])[C:11]=2[O:23]COC)=[O:9])[CH:7]=1.B(Br)(Br)Br.[Cl-].[NH4+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.C(#N)C.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:23][C:11]1[C:12]([F:22])=[N:13][C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:15][C:10]=1[C:8]2=[O:9]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 67383169(5-Bromo-2-fluorophenyl)(2-fluoro-3-(methoxymethoxy)-6-(neopentyloxy)pyridin-4-yl)methanone

생성물 1

HCID 673828597-bromo-1-fluoro-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one수율 78.6%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

실험 절차

A solution of (5-bromo-2-fluorophenyl)(2-fluoro-3-(methoxymethoxy)-6-(neopentyloxy)pyridin-4-yl)methanone (1.89 g, 4.25 mmol) in DCM (20 mL) was cooled to −78° C. under nitrogen atmosphere. Boron tribromide (1.0M in CH2Cl2; 4.25 mL, 4.25 mmol) was added drop wise and the reaction mixture was stirred for 5 min at rt. Aqueous, saturated ammonium chloride solution was added, followed by water and DCM. The organic phase was separated and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford a yellow solid, which was dissolved in ACN (20.00 mL). Cesium carbonate (1.386 g, 4.25 mmol) was added in one portion and the reaction mixture was allowed to stir for 5 min. Water was added and the remaining light-yellow solid was filtered off and dried to afford 7-bromo-1-fluoro-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one (1.27 g).

후처리

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customto afford a yellow solid, which
  5. stirringto stir for 5 min
  6. filtrationthe remaining light-yellow solid was filtered off
  7. customdried

출처 및 근거

ORD 기록
ord-00c5125f7aa044e5b708969161754882
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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