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

反応式

HRID 335906 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7adc4084163f4c1cadac176ab53a7001
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

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