Potassium Carbonate → Ethyl 4-ethoxy-1-pent-3-ynyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 1252699노트

반응식

HRID 1252699 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:15][CH2:16][CH3:17])=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][C:27]#[C:28][CH3:29]>CN(C=O)C>[CH2:16]([O:15][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][N:10]=[C:9]2[N:12]([CH2:29][CH2:28][C:27]#[C:26][CH3:25])[N:13]=[CH:14][C:8]=12)[CH3:17]

참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 124762055-Bromopent-2-yne2회HCID 14590535CID 14590535

생성물 1

HCID 14590534Ethyl 4-ethoxy-1-pent-3-ynyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of the ethyl-4-ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate of Example 19c (8.13 g.), pulverized anhydrous potassium carbonate (14.3 g.) and 1-bromo-3-pentyne (10.7 g.) in dry DMF (58 ml.) was stirred at 55°-60° for 4.5 hours. Additional quantities of 1-bromo-3-pentyne (5.3 g.) and potassium carbonate (14.3 g.) were added after 1 hour. The mixture was cooled and filtered and the filtrate evaporated at 45°-50°. The residue was diluted with water and extracted with ether and EtOAc. The combined extracts were washed with water, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel using EtOAc/hexane 1:1 v/v as eluant to give the title compound, m.p. 93°-95°, after recrystallization from toluene.

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated at 45°-50°
  4. additionThe residue was diluted with water
  5. extractionextracted with ether and EtOAc
  6. washThe combined extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-1f7c08d7c64d4cbfa576e85975811ba1
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04745121

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