Potassium Carbonate → HCID 67389134, compound

HRID 908474Notes

Reaction equation

HRID 908474 reaction equation
[Br:1][C:2]1[C:3]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])=[N:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)(=O)=O>C(#N)C>[Br:1][C:2]1[C:3]([C:7](=[O:8])[N:9]([CH3:11])[CH3:10])=[N:4][N:5]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178484499HCID 178484499, compound

Product 1

HCID 67389134HCID 67389134, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-bromo-N,N-dimethyl-1H-pyrazole-3-carboxamide (450 mg), potassium carbonate (456 mg) and tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (900 mg) in acetonitrile (13 mL) were stirred at 90° C. overnight. The mixture was concentrated and the residue was dissolved in ethylacetate, washed with water, brine dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 50 to 90% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford tert-butyl 4-[4-bromo-3-(dimethylcarbamoyl)pyrazol-1-yl]piperidine-1-carboxylate (340 mg). NMR Spectrum: (DMSOd6) 1.41 (s, 9H), 1.73 (dd, 1H), 1.78 (dd, 1H), 1.96-1.05 (m, 2H), 2.89 (bs, 2H), 2.95 (s, 3H), 2.87 (s, 3H), 3.92-4.10 (m, 2H), 4.33-4.44 (m, 1H), 8.15 (s, 1H); Mass spectrum: M+H+ 401-403

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethylacetate
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel eluting with 50 to 90% ethyl acetate in petroleum ether
  7. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-457ca3ec1398438f89f8c69d7368e578
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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