Potassium Carbonate → N-((6-bromobenzo[b]thiophen-3-yl)methyl)-N-methylmethanesulfonamide

HRID 2360053Notes

Reaction equation

HRID 2360053 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8](C(OCC)=O)[S:7][C:6]=2[CH:15]=1.[CH3:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19].[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:16][N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[CH:8][S:7][C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97632N-MethylmethanesulfonamideHCID 13567982Ethyl 6-bromo-1-benzothiophene-2-carboxylate

Product 1

HCID 67066523N-((6-bromobenzo[b]thiophen-3-yl)methyl)-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from Example 76, Part D (0.100 g, 0.382 mmol), N-methylmethane-sulfonamide (45.9 mg, 0.421 mmol) and potassium carbonate (0.127 g, 0.918 mmol) in N,N-dimethylacetamide (5 mL). The mixture was stirred at 80° C. for 11 h, cooled to room temperature and partitioned between diethylether and water (3×), dried over mgSO4, filtered and concentrated in vacuo to give the title compound as a colorless waxy solid (0.128 g, quant.).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between diethylether and water (3×)
  3. customdried over mgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c26e3c5159d647e0a39a174b6320d17e
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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