Potassium Carbonate → HCID 70869096, compound

HRID 1844706Notes

Reaction equation

HRID 1844706 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.Br[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].[H-].[Na+]>CN(C=O)C>[CH:14]1([CH2:13][N:6]2[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]2[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 965981H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl esterHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 70869096HCID 70869096, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 5-methyl-1H-pyrrole-2-carboxylate (15.0 g, 98.0 mmol), (bromo-methyl)cyclohexane (17.6 g, 100 mmol) and K2CO3 (41.4 g, 300 mmol) in dry DMF (150 mL) was stirred at 50° C. overnight, then cooled to rt and filtered. To the filtrate was added NaH (12.0 g, 60%, 300 mmol) slowly. Then the mixture was stirred overnight at 50° C. The reaction mixture was quenched with water and extracted with EA twice. The combined organic phases were washed with water (3×) and brine (2×), dried over Na2SO4, filtered, concentrated and purified by CC (EA/PE=1/20) to give compound 1a (19.9 g, 82%) as a white solid.

Workup

  1. filtrationfiltered
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EA twice
  4. washThe combined organic phases were washed with water (3×) and brine (2×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CC (EA/PE=1/20)

Sources & evidence

ORD record
ord-0a8e1da8068f45378b1141557e864230
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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