Cesium carbonate → HCID 69449216, compound

HRID 1517165Notes

Reaction equation

HRID 1517165 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:24])(=[O:23])[NH:11][CH:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:13]([CH3:15])[CH3:14])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39]Cl)[CH:34]=1.CCOC(C)=O.CCCCCC>CN(C)C=O>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:24])(=[O:23])[N:11]([CH:12]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH:13]([CH3:15])[CH3:14])[CH2:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 21226206Ethyl acetate hexaneHCID 69451353HCID 69451353, compound2×

Product 1

HCID 69449216HCID 69449216, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 4-(1-tert-Butoxycarbonyl-2-methyl-propylsulfamoyl)-benzoic acid methyl ester (Compound 1*—884 mg, 2.38 mmol) in dimethylformamide (30 ml) at ambient temperature was added cesium carbonate (10.86 g, 33.34 mmol). Then 3-picolyl chloride hydrochloride (546 mg, 3.33 mmol) was added to the suspension and the reaction mixture was stirred at room temperature for 24 hours by which time TLC (EtOAc/Hexane 1:1) monitoring showed the reaction to be completed. The mixture was evaporated to dryness and the residue was stirred in ethyl acetate (50 ml). The ethyl acetate phase was extracted with water (1×50 ml), dried (MgSO4), filtered and evaporated to afford the crude product as a brown oil. This oil was purified by flash chromatography to furnish the pure product as colourless oil.

Workup

  1. customthe reaction
  2. customThe mixture was evaporated to dryness
  3. extractionThe ethyl acetate phase was extracted with water (1×50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto afford the crude product as a brown oil
  8. customThis oil was purified by flash chromatography

Sources & evidence

ORD record
ord-84b71a53fe3045aa8c0d9410361717a7
Source dataset
uspto-grants-2012_07
Patent number
US08231858B2

Reaction notes

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