Tetrahydrofuran → HCID 178515146、化合物

HRID 222267ノート

反応式

HRID 222267 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.C1C[O:24]CC1>O.C(O)(=O)C.OO.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([OH:24])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

参加物

7

反応物 2

HCID 8028TetrahydrofuranHCID 67364710(3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)boronic acid

生成物 1

HCID 178515146HCID 178515146、化合物

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 784Hydrogen Peroxide溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

(3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)boronic acid (1.00 g, 3.5 mmol) was dissolved in a 0° C. solution of 25 mL of THF, 25 mL of water, 0.5 mL of acetic acid and 0.5 mL of 30% (w/w) hydrogen peroxide. The solution was stirred and allowed to warm to ambient temperature. After 6 h, the reaction mixture was partially concentrated and dissolved in 500 mL ethyl acetate. The organic layer was washed with water (2×100 mL), dried with magnesium sulfate, filtered, and concentrated to afford solids. The solids were dissolved in 20 mL dichloromethane and 60 mL hexanes and stirred as solids crystallized from the solution. After 2 hours, the crystalline solids were filtered and dried to afford the title compound. 1H NMR (600 MHz, DMSO-D6) δ 10.50 (s, 1H); 8.93 (s, 1H); 8.45 (s, 1H); 7.68 (d, 1H); 7.58 (d, 1H); 7.39 (d, 1H); 7.23 (d, 1H); 7.12 (d, 1H). LRMS (APCI) calculated for C14H9ClNO2 [M+H]+, 258.0; found 258.1.

後処理

  1. concentrationthe reaction mixture was partially concentrated
  2. dissolutiondissolved in 500 mL ethyl acetate
  3. washThe organic layer was washed with water (2×100 mL)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford solids
  8. customcrystallized from the solution
  9. waitAfter 2 hours
  10. filtrationthe crystalline solids were filtered
  11. customdried

出典と根拠

ORDレコード
ord-62c8398e57ef411fb3cc49f4684102df
出典データセット
uspto-grants-2012_06
特許番号
US08207186B2

反応ノート

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