Acetyl chloride → 4-Hydroxymethylpyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester

HRID 2039773Notes

Reaction equation

HRID 2039773 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH2:6][C:7]1[C:8]2[N:9]([N:13]=[C:14]([C:16](O)=[O:17])[CH:15]=2)[CH:10]=[CH:11][CH:12]=1.C([O-])(O)=O.[Na+]>C(O)C>[CH2:1]([O:3][C:16]([C:14]1[CH:15]=[C:8]2[C:7]([CH2:6][OH:5])=[CH:12][CH:11]=[CH:10][N:9]2[N:13]=1)=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 671135914-Hydroxymethylpyrazolo[1,5-a]pyridine-2-carboxylic acid

Product 1

HCID 595389604-Hydroxymethylpyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Acetyl chloride (9.5 mL, 130 mmol) is added to absolute ethanol (200 mL). After 30 min, the solution is poured into the flask containing 4-hydroxymethyl-pyrazolo[1,5-a]pyridine-2-carboxylic acid. The mixture is warmed to 50° C. for 3.5 h. After cooling to rt, the mixture is made basic with dropwise addition of sat. aq. NaHCO3. The volatiles are removed under reduced pressure. The aqueous solution is extracted with EtOAc. The organics are dried over Na2SO4, filtered, and concentrated to afford the title compound as a tan powder. LC-MS m/z (M+Na+): 242.98§.

Workup

  1. additionthe solution is poured into the flask
  2. temperatureAfter cooling to rt
  3. customThe volatiles are removed under reduced pressure
  4. extractionThe aqueous solution is extracted with EtOAc
  5. dry with materialThe organics are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5d961a3c22bc4fd7a130f57abc642c19
Source dataset
uspto-grants-2013_11
Patent number
US08580812B2

Reaction notes

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