Potassium Carbonate → HCID 59389335, compound

HRID 2357892Notes

Reaction equation

HRID 2357892 reaction equation
C(OCCBr)(=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:14]([O:16][C:17]([C:19]1[C:20]([S:36][CH3:37])=[N:21][N:22]2[CH:27]=[C:26]([CH2:28][O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)[CH:25]=[CH:24][C:23]=12)=[O:18])[CH3:15]>C(Cl)(Cl)Cl>[CH2:14]([O:16][C:17]([C:19]1[C:20]([S:36][CH3:37])=[N:21][N:22]2[CH:23]=[CH:24][CH:25]=[C:26]([CH2:28][O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)[C:27]=12)=[O:18])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 68461207HCID 68461207, compound

Product 1

HCID 59389335HCID 59389335, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The compound of Example 14 (45.6 g) was dissolved in ethanol (500 mL). To this solution, carbon disulfide (10.3 mL) and dimethylsulfuric acid (16.3 mL) were added. An aqueous solution (100 mL) of potassium hydroxide (14.5 g) was then slowly added dropwise over 1.5 hours. Subsequently, ice water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4) to give a yellow oil (6.78 g). The oily product (8.64 g) was dissolved in chloroform (200 mL). To this solution, bromoethyl acetate (6.66 mL) was added and the resulting mixture was stirred for 6 hours at room temperature. Subsequently, the solvent was evaporated and the residue was washed with diethyl ether to give a yellow oil. The oily product was dissolved in chloroform (290 mL). To the solution, potassium carbonate (20.0 g) was added and the resulting mixture was stirred for 16 hours at room temperature. Subsequently, the mixture was filtered and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=8:1) gave an inseparable mixture of the title compound and 3-ethoxycarbonyl-2-methylthio-6-(tetrahydropyrane-2-yl oxymethyl)-pyrazolo[1,5-a]pyridine as a yellow oil (3.71 g, 0.6:1).

Workup

  1. customSubsequently, the solvent was evaporated
  2. washthe residue was washed with diethyl ether
  3. customto give a yellow oil
  4. stirringthe resulting mixture was stirred for 16 hours at room temperature
  5. filtrationSubsequently, the mixture was filtered
  6. customthe solvent was evaporated
  7. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=8:1)
  8. customgave

Sources & evidence

ORD record
ord-50d45b7126ef49a3997dc0d4fa05b7b4
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

Loading…