Methyl chloroformate → methyl 3-acetyl-1H-indazole-1-carboxylate

HRID 922462Notes

Reaction equation

HRID 922462 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:12])[CH3:11])=[N:2]1.C(N(CC)CC)C.[C:20](Cl)(=[O:23])[O:21][CH3:22]>C(Cl)(Cl)Cl>[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([C:20]([O:21][CH3:22])=[O:23])[N:2]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 156841691-(1H-indazol-3-yl)ethan-1-one

Product 1

HCID 68309961methyl 3-acetyl-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-(1H-indazol-3-yl)ethanone (5.0 g) and triethylamine (6.53 mL) in chloroform (80 mL) was added dropwise a solution of methyl chlorocarbonate (3.24 g) in chloroform (20 mL) under ice-cooling over 1 hour, and the mixture was stirred at room temperature for 14 hours. The reaction solution was washed with aqueous saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated tinder reduced pressure. The resulting residue was triturated with n-hexane to give methyl 3-acetyl-1H-indazole-1-carboxylate) [REx(101-1)] (6.67 g) as a colorless powder.

Workup

  1. temperaturecooling over 1 hour
  2. washThe reaction solution was washed with aqueous saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated tinder reduced pressure
  5. customThe resulting residue was triturated with n-hexane

Sources & evidence

ORD record
ord-6e41ab7899e74a6d8ef9f17a35ad4ac5
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

Loading…