Phosphorus oxychloride → ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 606025Notes

Reaction equation

HRID 606025 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][CH:9]=[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11](OCC)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].P(Cl)(Cl)([Cl:23])=O>>[CH2:19]([O:18][C:16]([C:10]1[C:11]([Cl:23])=[C:6]2[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]2=[N:8][CH:9]=1)=[O:17])[CH3:20]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12845080Diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate

Product 1

HCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Conditions

Temperature
115 °C

Procedure

A mixture of diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate (2.5 g, 0.009 mole) and phosphorous oxy chloride (17.7 ml, 0.185 mole) was heated at 110-120° C. under stirring for about 3 hours under argon atmosphere. The reaction mixture was poured into ice water. It was extracted with dichloromethane and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give pure white solid compound. Yield: 1.8 g. m/z: (M++1) 253.9.

Workup

  1. extractionIt was extracted with dichloromethane
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give pure white solid compound

Sources & evidence

ORD record
ord-8a30d20f6a5c4e21aad8b2b98d9e55ee
Source dataset
uspto-grants-2011_03
Patent number
US07915286B2

Reaction notes

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