Bromide ion → HCID 57640482, compound

HRID 388794Notes

Reaction equation

HRID 388794 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][NH:14][C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:16])[O:10][N:9]=2)=[CH:4][CH:3]=1.[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[Br-]>O1CCOCC1.[Cu]I.CS(C)=O>[Cl:22][C:19]1[S:18][C:17]([C:15]([NH:14][CH2:13][CH:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]4=[O:23])=[CH:3][CH:4]=3)[CH2:12]2)=[O:16])=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 259Bromide ionHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 11582095HCID 11582095, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 57640482HCID 57640482, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Aryl bromide (Example 1, 100 mg, 0.25 mmol) and 2-hydroxypyridine (95 mg, 1.0 mmol) were dissolved in 1.5 mL dry dioxane and 0.5 mL dry DMSO in a sealed tube. To it were added N,N′-dimethylethylenediamine (27 μL, 0.25 mmol), CuI (95 mg, 0.125 mmol) and K3PO4 (106 mg, 0.5 mmol) in order. The mixture was stirred and heated in 120° C. bath till all the bromide starting material had been consumed (3 hrs, monitored by analytical HPLC). The mixture was filtered and directly subjected to reverse phase preparative HPLC to isolate the title compound as a white powder after lyophilization. MS found for C20H16ClN3O3S as (M+H)+ 414.1, 416.1

Workup

  1. customhad been consumed (3 hrs, monitored by analytical HPLC)
  2. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-7fa66dd937e14c21b96775b42ffef098
Source dataset
uspto-grants-2013_02
Patent number
US08377974B2

Reaction notes

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