Cesium carbonate → HCID 66895718, compound

HRID 633133Notes

Reaction equation

HRID 633133 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-1972b8779599417bb4edb2eef7fe9110
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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