Sodium Carbonate → HCID 53246857, compound

HRID 1189587Notes

Reaction equation

HRID 1189587 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:11]1[C:15]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)(=[O:25])=[O:24])=[C:14]([CH3:31])[N:13]([CH2:32][C:33]([O:35][CH2:36]C)=[O:34])[C:12]=1[CH3:38].C(=O)([O-])[O-].[Na+].[Na+]>CO.C1(C)C=CC=CC=1>[CH3:38][C:12]1[N:13]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:14]([CH3:31])=[C:15]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([N:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)(=[O:25])=[O:24])[C:11]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2×HCID 53246739HCID 53246739, compound

Product 1

HCID 53246857HCID 53246857, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of phenylboronic acid (26.9 mg, 0.221 mmol) in methanol (1.0 mL) and toluene (1.0 mL) was added ethyl 2-(3-iodo-2,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)phenylthio)-1H-pyrrol-1-yl)acetate (121 mg, 0.221 mmol), palladium tetrakistriphenylphosphine (12.8 mg, 0.0110 mmol) and sodium carbonate (0.090 mL, 0.18 mmol). The reaction mixture was heated at 100° C. for 2.5 hours, then heated at 60° C. for 16 hours, after which an additional 0.10 equiv. of both phenylboronic acid and palladium tetrakistriphenylphosphine were added. The reaction was then heated at 100° C. for one more hour, after which it was allowed to cool down to room temperature, poured over ice water (10 mL), extracted with ether (2×20 mL), and washed with water (1×30 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated. Purification by column chromatography on silica gel afforded methyl 2-(2,5-dimethyl-3-phenyl-4-(2-(pyrrolidin-1-ylsulfonyl)phenylthio)-1H-pyrrol-1-yl)acetate (0.0246 g, 0.0510 mmol, 23% yield) as a light brown residue. LCMS: ES+ [M+H]+=485.3

Workup

  1. temperatureheated at 60° C. for 16 hours
  2. temperatureThe reaction was then heated at 100° C. for one more hour
  3. temperatureto cool down to room temperature
  4. extractionextracted with ether (2×20 mL)
  5. washwashed with water (1×30 mL)
  6. dry with materialThe combined organic layers were dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-ea3f4949ba76463287c98577d76413e9
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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