Potassium Phosphate, Tribasic → HCID 86623909、化合物

HRID 1666464ノート

反応式

HRID 1666464 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)[CH:16]=1)[CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9].[CH:28]1(B(O)O)[CH2:30][CH2:29]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1>[CH:28]1([C:2]2[CH:3]=[C:4]([CH:14]=[C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=3)[CH:16]=2)[CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])[CH2:30][CH2:29]1

参加物

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 86623908Diethyl 3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylphosphonate

生成物 1

HCID 86623909HCID 86623909、化合物収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of diethyl 3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylphosphonate (0.93 g, 1.99 mmol) and cyclopropylboronic acid (0.204 g, 2.38 mmol) in THF (5.6 mL) was added potassium phosphate (1.27 g, 5.99 mmol). The mixture was degassed by purging with argon. PdCl2(dppf2 (162.2 mg, 0.198 mmol) and water (0.11 mL) were added to the reaction mixture and the mixture was degassed again. The reaction was heated at 50° C. for 1 h. The reaction mixture was concentrated and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel column chromatography (20% ethyl acetate in hexane) to give the title compound (0.8 g, 94%). 1H NMR (500 MHz, CDCl3): δ 8.42 (s, 1H), 7.87 (d, J=8.5 Hz, 1H), 6.96 (d, J=9 Hz, 1H), 6.90 (s, 1H), 6.86 (s, 1H), 6.73 (s, 1H),), 4.02 (m, 4H), 3.14 (s, 1H), 3.10 (s, 1H), 1.87 (m, 1H), 1.24 (m, 6H), 0.96 (d, J=8.5 Hz, 2H), 0.69 (d, J=5 Hz, 2H); m/z (430.0, M+ H+).

後処理

  1. customThe mixture was degassed
  2. customby purging with argon
  3. additionPdCl2(dppf2 (162.2 mg, 0.198 mmol) and water (0.11 mL) were added to the reaction mixture
  4. customthe mixture was degassed again
  5. concentrationThe reaction mixture was concentrated
  6. extractionextracted with ethyl acetate three times
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness
  10. customThe residue was purified by silica gel column chromatography (20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-69232c2e6f6945179fb56030cc6c86cd
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

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