Sodium Bicarbonate → N-(3-ethylphenyl)-1-[(2E)-3-(3-{[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]oxy}phenyl)prop-2-enyl]-1H-pyrrole-2-carboxamide

HRID 1352874Notes

Reaction equation

HRID 1352874 reaction equation
CC1C=CC(S([O:11][C@H:12]([CH3:21])[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])(=O)=O)=CC=1.[CH2:22]([N:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH3:40])[CH:34]=1)=[O:31])[CH:23]=[CH2:24].C(=O)([O-])O.[Na+].S([O-])(O)(=O)=O.[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:39]([C:35]1[CH:34]=[C:33]([NH:32][C:30]([C:26]2[N:25]([CH2:22]/[CH:23]=[CH:24]/[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([O:11][C@@H:12]([CH3:21])[C:13]([N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)=[O:14])[CH:34]=3)[CH:29]=[CH:28][CH:27]=2)=[O:31])[CH:38]=[CH:37][CH:36]=1)[CH3:40]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 10903086(1R)-1-methyl-2-morpholin-4-yl-2-oxoethyl 4-methylbenzenesulfonateHCID 229286871-allyl-N-(3-ethylphenyl)-1H-pyrrole-2-carboxamide

Product 1

HCID 69142288N-(3-ethylphenyl)-1-[(2E)-3-(3-{[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]oxy}phenyl)prop-2-enyl]-1H-pyrrole-2-carboxamideYield 173.3%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (1R)-1-methyl-2-morpholin-4-yl-2-oxoethyl 4-methylbenzenesulfonate (310 mg, 0.858 mmol), 1-allyl-N-(3-ethylphenyl)-1H-pyrrole-2-carboxamide (210 mg, 0.826 mmol), palladium acetate (10 mg, 0.045 mmol), sodium hydrogencarbonate (140 mg, 1.66 mmol) and benzyltriethylammonium chloride (190 mg, 0.834 mmol) in dimethylformamide (5 ml) was stirred for 3 hours at 50° C. Thereto was added an aqueous 5% potassium hydrogensulfate solution and the mixture was extracted with ethyl acetate/toluene(2/1). The organic layer was washed with water, an aqueous sodium thiosulfate solution and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=5:1→3:1) to give N-(3-ethylphenyl)-1-[(2E)-3-(3-{[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]oxy}phenyl)prop-2-enyl]-1H-pyrrole-2-carboxamide (349 mg, 83%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate/toluene(2/1)
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous sodium thiosulfate solution and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified with silica gel chromatography (hexane:ethyl acetate=5:1→3:1)

Sources & evidence

ORD record
ord-9fc7b192bfba47a9b953eb771a98f624
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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