Potassium Carbonate → 4-[(3-chloro-4-cyanophenoxy)methyl]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

HRID 1525649Notes

Reaction equation

HRID 1525649 reaction equation
Br[CH2:2][C:3]1[C:17]([F:18])=[CH:16][C:6]([C:7]([NH:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[O:8])=[C:5]([F:19])[CH:4]=1.[Cl:20][C:21]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:22]=1[C:23]#[N:24].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl.O>[Cl:20][C:21]1[CH:28]=[C:27]([CH:26]=[CH:25][C:22]=1[C:23]#[N:24])[O:29][CH2:2][C:3]1[C:17]([F:18])=[CH:16][C:6]([C:7]([NH:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[O:8])=[C:5]([F:19])[CH:4]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 896195864-(Bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

Product 1

HCID 716161464-[(3-chloro-4-cyanophenoxy)methyl]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide (Preparation 1, 33 mg, 0.092 mmol) in DMSO (1 mL) was added 2-chloro-4-hydroxybenzonitrile (114 mg, 0.092 mmol) and K2CO3 (25 mg, 0.18 mmol). The reaction was stirred at room temperature for 16 hours. The reaction was diluted with DCM (10 mL) and water (20 mL). The organic layer was separated and the aqueous layer extracted with DCM (2×10 mL). The combined organic layers were filtered through a phase separation cartridge and reduced to dryness to give a yellow oil which was purified by reverse phase preparative HPLC to afford the title compound.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with DCM (2×10 mL)
  3. filtrationThe combined organic layers were filtered through a phase separation cartridge
  4. customto give a yellow oil which
  5. customwas purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-5ea0b19e71e34514a5071bc35779f6c6
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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