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

HRID 1252699ノート

反応式

HRID 1252699 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium Carbonate2 回HCID 124762055-Bromopent-2-yne2 回HCID 14590535CID 14590535

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1f7c08d7c64d4cbfa576e85975811ba1
出典データセット
uspto-grants-1988_05
特許番号
US04745121

反応ノート

読み込み中…