Trifluoroacetic acid → HCID 18369481, compound

HRID 1699801Notes

Reaction equation

HRID 1699801 reaction equation
FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[CH3:15][C:16]1[CH:29]=[C:19]2[CH:20]=[C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:22]=[CH:23][N:18]2[N:17]=1.[Cl:30][C:31]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:32]=1[CH:33]=O>ClCCl>[Cl:30][C:31]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:32]=1[CH2:33][C:29]1[C:16]([CH3:15])=[N:17][N:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][C:19]=12

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 134042,4-Dichlorobenzaldehyde2×HCID 22388192HCID 22388192, compound

Product 1

HCID 18369481HCID 18369481, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of trifluoroacetic acid (558 mg) and triethylsilane (1.14 g) in dry dichloromethane (2.0 ml) were added ethyl 2-methylpyrazolo[1,5-a]pyridine-5-carboxylate (200 mg) and 2,4-dichlorobenzaldehyde (189 mg), and the mixture was stirred at room temperature for 3 days. To the reaction mixture was added 2,4-dichlorobenzaldehyde (189 mg) and the mixture was stirred at room temperature for one day. This step was repeated three times. The reaction mixture was diluted with dichloromethane and washed with a saturated aqueous sodium hydrogencarbonate solution. The aqueous layer was extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9:1) and washed with isopropyl ether to give the objective compound (233 mg) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for one day
  2. washwashed with a saturated aqueous sodium hydrogencarbonate solution
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9:1)
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-10b83fe2f4b24c7ab49ef0b7cd22fb10
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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