Dimethyl Sulfoxide → 5-fluoro-2-methyl-2H-indazole-4-carbaldehyde

HRID 1639780Notes

Reaction equation

HRID 1639780 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[CH:20]=[CH:19][C:18]2[C:14](=[CH:15][N:16]([CH3:21])[N:17]=2)[C:13]=1[CH2:22][OH:23].C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:20]=[CH:19][C:18]2[C:14](=[CH:15][N:16]([CH3:21])[N:17]=2)[C:13]=1[CH:22]=[O:23]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59334543(5-fluoro-2-methyl-2H-indazol-4-yl)methanol

Product 1

HCID 593346015-fluoro-2-methyl-2H-indazole-4-carbaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethyl sulfoxide (7.56 mL, 107 mmol) in dichloromethane (100 mL) was added oxalyl chloride (4.86 mL, 53.3 mmol) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added a solution of (5-fluoro-2-methyl-2H-indazol-4-yl)methanol (3.20 g, 17.8 mmol) in dichloromethane (78.0 mL), and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (22.5 mL, 160 mmol) at −78° C., and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/3) to give the title compound (3.00 g, yield 95%).

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. stirringthe mixture was stirred for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-f97a68c6b1ff46e485745a6a401d364a
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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