Benzeneethanamine, alpha-methyl-, phosphate (1:1) → 2-fluoro-7-(2-fluoropyridin-3-yl)-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one

HRID 335906

반응식

HRID 335906 반응식
Br[C:2]1[CH:3]=[C:4]2[C:27](=[CH:28][CH:29]=1)[O:26][C:7]1=[N:8][C:9]([F:25])=[C:10]([Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:11]=[C:6]1[C:5]2=[O:30].CC(N)CC1C=CC=CC=1.OP(O)(O)=O.C([O-])(=O)C.[K+].[F:51][C:52]1[C:57](B(O)O)=[CH:56][CH:55]=[CH:54][N:53]=1>CCO.O.C(OCC)(=O)C>[F:25][C:9]1[N:8]=[C:7]2[O:26][C:27]3[C:4]([C:5](=[O:30])[C:6]2=[CH:11][C:10]=1[Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:3][C:2]([C:57]1[C:52]([F:51])=[N:53][CH:54]=[CH:55][CH:56]=1)=[CH:29][CH:28]=3

참가 물질

8

반응물 4

HCID 62885Benzeneethanamine, alpha-methyl-, phosphate (1:1)HCID 517044Potassium AcetateHCID 27832702-Fluoropyridine-3-boronic acidHCID 673833207-bromo-2-fluoro-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one

생성물 1

HCID 673827952-fluoro-7-(2-fluoropyridin-3-yl)-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

7-Bromo-2-fluoro-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one (0.240 g, 0.412 mmol), AmPhos (0.015 g, 0.021 mmol), potassium acetate (0.077 mL, 1.235 mmol), and 2-fluoro-3-pyridineboronic acid (0.070 g, 0.494 mmol) were suspended in a mixture of EtOH (20 mL) and water (2 mL) and heated to 85° C. After 30 minutes water (250 mL) and ethyl acetate (200 mL) were added and the phases mixed and separated. The organic was washed with 10% saturated sodium bicarbonate (100 mL) then dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude was purified using silica chromatography (hexane to ethyl acetate gradient) to give 2-fluoro-7-(2-fluoropyridin-3-yl)-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one.

후처리

  1. additionthe phases mixed
  2. customseparated
  3. washThe organic was washed with 10% saturated sodium bicarbonate (100 mL)
  4. dry with materialthen dried with magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude was purified

출처 및 근거

ORD 기록
ord-7adc4084163f4c1cadac176ab53a7001
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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