Acetyl chloride → Acetic acid 7-allyl-1H-indazol-6-yl ester

HRID 2121857Notes

Reaction equation

HRID 2121857 reaction equation
[CH2:1]([C:4]1[C:5]([OH:13])=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[CH:9]2)[CH:2]=[CH2:3].C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>C1COCC1>[CH2:1]([C:4]1[C:5]([O:13][C:21](=[O:23])[CH3:22])=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[CH:9]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6367Acetyl chloride3×HCID 8471TriethylamineHCID 1358436477-Allyl-1H-indazol-6-ol

Product 1

HCID 69566045Acetic acid 7-allyl-1H-indazol-6-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Step B (6.35 g, 37 mmol) in THF (100 mL) containing triethylamine (7.6 ml, 55 mmol) was stirred for 5 minutes at ambient temperature, cooled to 0° C. (ice bath), and acetyl chloride (2.63 mL, 37 mmol) was added. The mixture was stirred at 0° C. for 2 hours, additional acetyl chloride (0.26 mL, 3.7 mmol) was added, and the mixture stirred for 10 min at which point another portion of acetyl chloride (0.26 ml, 3.7 mmol) was added and stirring continued for 15 min. The reaction was quenched with triethyl amine (1 mL) and saturated aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (100 mL). The extract was dried (MgSO4) and evaporated to an oil (9.27 g) which was purified by chromatography (silica, 10% to 50% EtOAc/hexane) to give a white solid, (3.50 g, 44%): LC/MS (+APCI) m/z 217 (M+H).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at 0° C. for 2 hours
  3. additionwas added
  4. stirringstirring
  5. waitcontinued for 15 min
  6. customThe reaction was quenched with triethyl amine (1 mL) and saturated aqueous sodium bicarbonate (100 mL)
  7. extractionextracted with ethyl acetate (100 mL)
  8. dry with materialThe extract was dried (MgSO4)
  9. customevaporated to an oil (9.27 g) which
  10. customwas purified by chromatography (silica, 10% to 50% EtOAc/hexane)
  11. customto give a white solid, (3.50 g, 44%)

Sources & evidence

ORD record
ord-dd3c88a898294c168d54ab848edfed13
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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