Dimethyl Sulfoxide → 2-Methylpyrazolo[1,5-A]pyridine-4-carbaldehyde

HRID 1639744Notes

Reaction equation

HRID 1639744 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH:22]=[C:15]2[C:16]([CH2:20][OH:21])=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1.C(N(CC)CC)C>ClCCl>[CH3:11][C:12]1[CH:22]=[C:15]2[C:16]([CH:20]=[O:21])=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59334539(2-Methylpyrazolo[1,5-a]pyridin-4-yl)methanol

Product 1

HCID 593346342-Methylpyrazolo[1,5-A]pyridine-4-carbaldehydeYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere, to a solution of oxalyl chloride (18.9 mL, 216 mmol) in dichloromethane (200 mL) was added dimethyl sulfoxide (35.4 mL, 499 mmol) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added a solution of (2-methylpyrazolo[1,5-a]pyridin-4-yl)methanol (27.0 g, 166 mmol) in dichloromethane (133 mL), and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (117 mL, 831 mmol) at −78° C., and the mixture was stirred for 1 hr and warmed to room temperature. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to give the title compound (7.00 g, yield 26%).

Workup

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

Sources & evidence

ORD record
ord-bc2e118a8810468ba34705b747550c87
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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