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

HRID 2113788노트

반응식

HRID 2113788 반응식
[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

참가 물질

5

반응물 3

HCID 176Acetic Acid2회HCID 6096233Potassium diazene-1,2-dicarboxylate2회HCID 598115207-(2,4-dichloro-phenyl)-2-methyl-3-vinyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d7424b7128e4dca895cce1735779b69
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432283B2

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