Cesium carbonate → HCID 136413571, compound

HRID 1050777Notes

Reaction equation

HRID 1050777 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:28])=[C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:19][S:18][C:9]2=[C:10]([C:12]#[C:13][Si](C)(C)C)[N:11]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+]>CCO.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:28])=[C:8]2[C:20]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:19][S:18][C:9]2=[C:10]([C:12]#[CH:13])[N:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 136344026HCID 136344026, compound

Product 1

HCID 136413571HCID 136413571, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of 3-(4-chloro-phenyl)-4-hydroxy-7-trimethylsilanylethynyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (0.189 mmol) in EtOH/CH2Cl2 (1/1, 0.76 mL) was added Cs2CO3 (0.227 mmol) with stirring at r.t. After 16 h the mixture was partitioned between 1N HCl (10 mL) and EtOAc (10 mL). The aqueous phase was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine and water, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 0-20% EtOAc/CH2Cl2, to give the title compound (38 mg) as a white solid: MS (m/z) 357.0 (M−1).

Workup

  1. customAfter 16 h the mixture was partitioned between 1N HCl (10 mL) and EtOAc (10 mL)
  2. extractionThe aqueous phase was extracted with EtOAc (2×10 mL)
  3. washThe combined organic layers were washed with brine and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-cef641c5513349c08b2bafe0b56725bc
Source dataset
uspto-grants-2016_07
Patent number
US09387200B2

Reaction notes

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