Cesium carbonate → HCID 66895718, compound

HRID 922982Notes

Reaction equation

HRID 922982 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:15][C:16]1[CH:25]=[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[N:4]1([CH2:3][CH2:2][N:26]([C:24]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([Cl:15])[CH:25]=2)[S:27]([CH3:30])(=[O:28])=[O:29])[CH:8]=[CH:7][CH:6]=[CH:5]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 116512251-(2-Bromoethyl)pyrroleHCID 54238017Methyl 2-chloro-4-(methylsulfonamido)benzoate

Product 1

HCID 66895718HCID 66895718, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 μL of 1-(2-bromoethyl)-1H-pyrrole and 556 mg of Cesium Carbonate were added to 150 mg of methyl 2-chloro-4-(methylsulfonamido)benzoate in DMF and stirred at room temperature for 16 hours. The reaction mixture was extracted in Ethyl Acetate twice with saturated bicarbonate and once with brine, dried over Magnesium Sulfate, filtered and concentrated to give methyl 4-(N-(2-(1H-pyrrol-1-yl)ethyl)methylsulfonamido)-2-chlorobenzoate. 230 mg of methyl 4-(N-(2-(1H-pyrrol-1-yl)ethyl)methylsulfonamido)-2-chlorobenzoate was hydrolyzed via Procedure M to yield 221 mg of crude 4-(N-(2-(1H-pyrrol-1-yl)ethyl)methylsulfonamido)-2-chlorobenzoic acid.

Workup

  1. extractionThe reaction mixture was extracted in Ethyl Acetate twice with saturated bicarbonate and once with brine
  2. dry with materialdried over Magnesium Sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b64a88ed87b446b69452cb5a9148b695
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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