Potassium Carbonate → HCID 118037923, compound

HRID 2272456Notes

Reaction equation

HRID 2272456 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]2)(=O)=O)=CC=1>COCCOC>[Br:7][C:8]1[CH:13]=[CH:12][N:11]([CH:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]2)[C:10](=[O:14])[CH:9]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 8171154-Bromo-2-hydroxypyridineHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 118037923HCID 118037923, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Potassium tert-butoxide (7.09 g) was added at room temperature to a mixture of 4-bromopyridin-2(1H)-one (10 g) in DME (287 mL). The reaction mixture was stirred at room temperature for 10 minutes. Then, potassium carbonate (15.9 g) and tert-butyl 4-(((4-methylphenyl)sulfonyl)oxy)piperidine-1-carboxylate (37.8 g) were added thereto, and the mixture was stirred at 85 C for 1 day, at 95 C for 1 day, and at 100 C for 1 day in a nitrogen atmosphere. Saturated saline was added to the reaction mixture, followed by extraction with ethyl acetate twice. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (14.7 g).

Workup

  1. stirringthe mixture was stirred at 85 C for 1 day, at 95 C for 1 day
  2. waitat 100 C for 1 day in a nitrogen atmosphere
  3. additionSaturated saline was added to the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate twice
  5. washThe obtained organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-373c29cd7ec8465ca436e9ecdf35a991
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

Loading…