Dimethyl Sulfoxide → HCID 59334530, compound

HRID 1639806Notes

Reaction equation

HRID 1639806 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[C:20]2[C:16](=[CH:17][N:18]([CH3:21])[N:19]=2)[C:15]([CH2:22][OH:23])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[F:11][C:12]1[C:20]2[C:16](=[CH:17][N:18]([CH3:21])[N:19]=2)[C:15]([CH:22]=[O:23])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59334607HCID 59334607, compound

Product 1

HCID 59334530HCID 59334530, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethyl sulfoxide (4.30 mL, 60.5 mmol) in dichloromethane (50 mL) was added oxalyl chloride (2.65 mL, 30.3 mmol) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added a solution of (7-fluoro-2-methyl-2H-indazol-4-yl)methanol (1.82 g, 10.1 mmol) in dichloromethane (51 mL), and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (12.8 mL, 91.0 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 silica gel column chromatography (ethyl acetate/hexane=1/3) to give the title compound (1.60 g, yield 89%).

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 silica gel column chromatography (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-dca64ea65418417fb8a8286443d2ee28
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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