Acetic Acid → 7-(2,4-Dichloro-phenyl)-3-ethyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine

HRID 2113788ノート

反応式

HRID 2113788 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][CH2:12][C:11]2=[C:15]([CH:19]=[CH2:20])[N:16]([CH3:18])[N:17]=[C:10]12.N(C([O-])=O)=NC([O-])=O.[K+].[K+].C(O)(=O)C>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][CH2:12][C:11]2=[C:15]([CH2:19][CH3:20])[N:16]([CH3:18])[N:17]=[C:10]12

参加物

5

反応物 3

HCID 176Acetic Acid2 回HCID 6096233Potassium diazene-1,2-dicarboxylate2 回HCID 598115207-(2,4-dichloro-phenyl)-2-methyl-3-vinyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine

生成物 1

HCID 598115237-(2,4-Dichloro-phenyl)-3-ethyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

実験手順

To a solution of 7-(2,4-dichloro-phenyl)-2-methyl-3-vinyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine (3-7; 0.046 g, 0.15 mmol) in 2 mL of methanol was added dipotassium azodicarboxylate (0.174 g, 0.90 mmol) [prepared according to D. J. Pasto and R. J. Taylor, Organic Reactions 1991 40:91]. To the yellow suspension was added acetic acid (0.102 mL, 1.80 mmol) in 2 mL of methanol over 40 minutes. The reaction mixture was again treated with dipotassium azodicarboxylate (0.087 g, 0.45 mmol) and then acetic acid (0.051 mL, 0.90 mmol) in 1 mL of methanol over 20 nm. After 3 h at room temperature, the solvent was evaporated, the residue was treated with 10 mL of saturated sodium bicarbonate solution, extracted three times with 25 mL portions of dichloromethane, dried over magnesium sulfate, and evaporated to afford 41 mg of crude product. The crude product was purified by silica gel column chromatography eluting with 0 to 15% ethyl acetate/hexane which afforded 30 mg (65% theory) of 4-6 as a colorless oil: ms (M+H)+=310.

後処理

  1. customthe solvent was evaporated
  2. additionthe residue was treated with 10 mL of saturated sodium bicarbonate solution
  3. extractionextracted three times with 25 mL portions of dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto afford 41 mg of crude product
  7. customThe crude product was purified by silica gel column chromatography
  8. washeluting with 0 to 15% ethyl acetate/hexane which

出典と根拠

ORDレコード
ord-4d7424b7128e4dca895cce1735779b69
出典データセット
uspto-grants-2008_10
特許番号
US07432283B2

反応ノート

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