Sodium Carbonate → HCID 58305696, compound

HRID 2362236Notes

Reaction equation

HRID 2362236 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]([C:17]4[CH:22]=[CH:21][C:20]([C:23](=O)[NH2:24])=[CH:19][C:18]=4[CH3:26])[C:15]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.O=P(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[N:16]([C:17]4[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][C:18]=4[CH3:26])[C:15]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 58305614HCID 58305614, compound

Product 1

HCID 58305696HCID 58305696, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (30A) (2.0 g, 4.52 mmol) in DMF (9 mL) was added POCl3 (693 mg, 4.52 mmol) at 0° C., and then stirred at room temperature for 1.5 h. After cooling to room temperature, the reaction mixture was added to ice-water (20 mL). Sat. Na2CO3 was added to adjust pH=8 followed by extraction with ethyl acetate (50 mL×4). The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (PE:EA=1:1) to afford ethyl 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (30B) (1.02 g, 53%), LC-MS: [M+H]+ 425.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with ethyl acetate (50 mL×4)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (PE:EA=1:1)

Sources & evidence

ORD record
ord-42b1968b2ce041ae949baf1e609662ae
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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