Potassium Carbonate → HCID 58208670, compound

HRID 38469Notes

Reaction equation

HRID 38469 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH:13]1([N:16]2[C:24]3[C:19](=[C:20]([OH:49])[CH:21]=[C:22]([C:25]([N:27]4[CH2:32][CH2:31][C:30]5([CH2:41][C:40](=[O:42])[C:39]6[C:34](=[CH:35][CH:36]=[C:37]([C:43]7[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=7)[CH:38]=6)[O:33]5)[CH2:29][CH2:28]4)=[O:26])[CH:23]=3)[CH:18]=[CH:17]2)[CH2:15][CH2:14]1>CN(C=O)C.CCOC(C)=O>[CH:13]1([N:16]2[C:24]3[C:19](=[C:20]([O:49][CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH:21]=[C:22]([C:25]([N:27]4[CH2:28][CH2:29][C:30]5([CH2:41][C:40](=[O:42])[C:39]6[C:34](=[CH:35][CH:36]=[C:37]([C:43]7[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=7)[CH:38]=6)[O:33]5)[CH2:31][CH2:32]4)=[O:26])[CH:23]=3)[CH:18]=[CH:17]2)[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 58208666HCID 58208666, compound

Product 1

HCID 58208670HCID 58208670, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl bromoacetate (0.059 ml, 0.604 mmol) was added to a stirred mixture of K2CO3 (111 mg, 0.806 mmol), 1′-[(1-cyclopropyl-4-hydroxy-1H-indol-6-yl)carbonyl]-6-(1-methyl-1H-pyrazol-4-yl)spiro[chroman-2,4′-piperidin]-4-one (200 mg, 0.403 mmol) in DMF (2 ml) and the mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc, washed with water, brine, and dried over MgSO4. After filteration and evaporation, the residue was purified by silicagel column chromatography (CHCl3/MeOH) to give intended compound as yellow oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customAfter filteration and evaporation
  4. customthe residue was purified by silicagel column chromatography (CHCl3/MeOH)
  5. customto give

Sources & evidence

ORD record
ord-da07b2982eef4157b5eae8c96570fe77
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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