Potassium Carbonate → HCID 68816860, compound

HRID 735559Notes

Reaction equation

HRID 735559 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:23])OC2C=CC=CC=2)[CH:6]=[CH:7][C:8]=1[S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])#[N:2].[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][NH:33][CH3:34])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][N:33]([CH3:34])[C:15]([NH:14][C:5]2[CH:6]=[CH:7][C:8]([S:9]([CH2:12][CH3:13])(=[O:10])=[O:11])=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:23])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 183675562-(4-Bromophenyl)-N-methylethan-1-amineHCID 68818495Phenyl 3-cyano-4-(ethylsulfonyl)phenylcarbamate

Product 1

HCID 68816860HCID 68816860, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 25A (750 mg, 2.3 mmol) and 23B (486 mg, 4.5 mmol) with potassium carbonate (627 mg, 2.3 mmol) in DMF (6 mL) were heated at 50° C. for 15 h. The mixture was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The organics were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield give 25B (950 mg, 93%) as a colorless oil. MS (ESI) m/z 449.89/451.91 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes)
  6. customto yield

Sources & evidence

ORD record
ord-e700c93d42414b1da260e5b6fb5360c0
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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