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

HRID 1966801Notes

Reaction equation

HRID 1966801 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][CH:9]=[C:10]([C:16](OCC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=[N:4]1)[CH3:2].P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:16]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:8]=[C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=12

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]methylidene}propanedioate (15 gm, 0.0533 mole) (example 2) and phosphorous oxy chloride (76.64 ml, 0.7998 mole) was heated at 110-120° C. under stirring for about 4 hours under argon atmosphere. The reaction mixture was cooled and then poured drop wise into ice water. A pale yellow solid separated which was filtered. The solid was first washed twice with ice cold water and then finally with hexane and dried over vacuum.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customA pale yellow solid separated which
  3. filtrationwas filtered
  4. washThe solid was first washed twice with ice cold water
  5. dry with materialfinally with hexane and dried over vacuum

Sources & evidence

ORD record
ord-312d6c314c554d95b25d5ab8d939ea65
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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