Potassium Carbonate → HCID 57561699, compound

HRID 1434823Notes

Reaction equation

HRID 1434823 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]([C:15]1[NH:16][CH:17]=[C:18]([CH:20]=O)[CH:19]=1)=[O:14])[CH3:11].C([BH3-])#N.[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.CO>[CH2:10]([O:12][C:13]([C:15]1[NH:16][CH:17]=[C:18]([CH2:20][N:6]([C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:7])[CH:19]=1)=[O:14])[CH3:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 702724-Chloro-N-methylbenzenamineHCID 321486Ethyl 4-formyl-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 57561699HCID 57561699, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

4-chloro-N-methylaniline (0.225 mL, 1.86 mmol) was added to a stirring, room temperature solution of 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.2585 g, 1.55 mmol) in 5% acetic acid in methanol under N2. After stirring at room temperature for 30 minutes, sodium cyanoborohydride (0.1585 g, 2.52 mmol) was added, and the reaction was stirred at room temperature overnight. About 3 mL of saturated K2CO3 were added, and the reaction was extracted twice with ethyl acetate. The combined organics were washed with saturated NaHCO3 (˜4 mL) and brine (˜4 mL), then the combined organics were dried with Na2SO4, filtered and concentrated en vacuo. The crude product was purified by silica gel chromatography (Combiflash column, 85:15 Hexanes:Ethyl acetate) to obtain 0.3419 g (76%) of 4-{[(4-chlorophenyl)-methylamino]methyl]-1H-pyrrole-2-carboxylic acid ethyl ester (191) as a light tan solid. Note: Starting material 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester has an HPLC retention time=7.337 min. HPLC: 8.478 min.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. extractionthe reaction was extracted twice with ethyl acetate
  3. washThe combined organics were washed with saturated NaHCO3 (˜4 mL) and brine (˜4 mL)
  4. dry with materialthe combined organics were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated en vacuo
  7. customThe crude product was purified by silica gel chromatography (Combiflash column, 85:15 Hexanes:Ethyl acetate)

Sources & evidence

ORD record
ord-dbb1214d0e0140119040c06cab4aff61
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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