Cyclopentanethiol → HCID 59516116, compound

HRID 1799425Notes

Reaction equation

HRID 1799425 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH:11]1([SH:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.Cl[C:18]1[N:22]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=2)[N:21]=[CH:20][C:19]=1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>CN(C=O)C.CCOC(C)=O>[CH:11]1([S:16][C:18]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)[N:21]=[CH:20][C:19]=2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 15510CyclopentanethiolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 57437894Tert-butyl 5-chloro-1-(4-methoxycarbonylphenyl)pyrazole-4-carboxylate2×

Product 1

HCID 59516116HCID 59516116, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Sodium bis(trimethylsilyl)amide (7.13 mL, 7.13 mmol) was added dropwise to cyclopentanethiol (0.761 mL, 7.13 mmol) in DMF (25 mL) under nitrogen. The resulting solution was stirred at 20° C. for 30 minutes. A solution of tert-butyl 5-chloro-1-(4-(methoxycarbonyl)phenyl)-1H-pyrazole-4-carboxylate (Intermediate #9) (2 g, 5.94 mmol) in DMF (10 mL) was then added dropwise and the resulting mixture was stirred at 20° C. for to 2 hours. The reaction mixture was diluted with EtOAc (200 mL), and washed sequentially with water (4×50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 5-(cyclopentylthio)-1-(4-(methoxycarbonyl)phenyl)-1H-pyrazole-4-carboxylate (1.380 g, 57.7%) as a colourless oil which crystallised on standing.

Workup

  1. stirringthe resulting mixture was stirred at 20° C. for to 2 hours
  2. washwashed sequentially with water (4×50 mL) and saturated brine (50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product
  7. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in isohexane
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-5b67cbf2d11a4bbdbc9f0022bd913914
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

Loading…