Cesium carbonate → HCID 58614719, compound

HRID 923094Notes

Reaction equation

HRID 923094 reaction equation
Br[CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:29]=[CH:28][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:16]=2)=[O:13])=[C:10]([Cl:30])[CH:9]=1)(=[O:7])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:4]([S:5]([C:8]1[CH:29]=[CH:28][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:16]=2)=[O:13])=[C:10]([Cl:30])[CH:9]=1)(=[O:7])=[O:6])[CH:3]=[CH2:2]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 668778424-(3-bromopropylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide

Product 1

HCID 58614719HCID 58614719, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

115 mg of NBS was added to a solution of 200 mg of 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(3-hydroxypropylsulfonyl)benzamide and 169 mg of triphenylphosphine in 3 mL of dichloromethane at 0° C. The reaction mixture was stirred at 0˜5° C. for 1 h. The mixture was diluted with dichloromethane, washed with H2O, dried (MgSO4) and evaporated. Purified by prep TLC plate (60% ethyl acetate/hexane) to afford 4-(3-bromopropylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. 60 mg of 4-(3-bromopropylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide and 111 mg of cesium carbonate in 0.5 mL of DMF were heated to 100° C. in a sealed microwave reactor for 20 min. The reaction mixture was evaporated, and the product was purified on reverse phase HPLC to yield 4-(allylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. MS (Q1) 448.0 (M)+.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe product was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-536908eccd29435dba64971b297b89c8
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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