Cesium carbonate → 2-(4-Fluoro-phenyl)-5-iodo-6-[methanesulfonyl-(3-methanesulfonyl-propyl)-amino]-furo[2,3-b]pyridine-3-carboxylic acid methylamide

HRID 2190166Notes

Reaction equation

HRID 2190166 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[C:11]([I:14])[CH:12]=2)[O:7][C:6]=1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[O:4].I[CH2:28][CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:15]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:28][CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])=[C:11]([I:14])[CH:12]=2)[O:7][C:6]=1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 580523242-(4-fluorophenyl)-5-iodo-N-methyl-6-(methylsulfonamido)furo[2,3-b]pyridine-3-carboxamideHCID 580525411-Iodo-3-methanesulfonylpropane

Product 1

HCID 580523692-(4-Fluoro-phenyl)-5-iodo-6-[methanesulfonyl-(3-methanesulfonyl-propyl)-amino]-furo[2,3-b]pyridine-3-carboxylic acid methylamideYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Fluoro-phenyl)-5-iodo-6-methanesulfonylamino-furo[2,3-b]pyridine-3-carboxylic acid methylamide (162 mg, 0.331 mmol), 1-iodo-3-(methylsulfonyl)propane (82 mg, 0.331 mmol) and cesium carbonate (119 mg, 0.364 mmol) in DMF (1656 μL) are heated for 20 min at 150° C. by microwave. 3:1 Product/starting material. An additional 45 mg of alky iodide are added and 60 mg of cesium carbonate and heated for 20 min at 150° C. by microwave. LCMS indicates complete consumption of starting material. Acetonitrile and water are added and the mixture is filtered with 0.45μ PTFE filter. Purification is achieved by reverse phase HPLC with a C8 column with 20-50% ACN//H2O (0.1% NH4OH) over 20 min. Elutes at 13-15 minutes to give the title compound (107 mg, 53%). MS (ESI) m/z 610.0 (M+1). Retention time=1.40 min, Method A.

Workup

  1. customconsumption of starting material
  2. additionAcetonitrile and water are added
  3. filtrationthe mixture is filtered with 0.45μ PTFE
  4. filtrationfilter
  5. customPurification

Sources & evidence

ORD record
ord-4b66339630f64375bf47f589135b9c79
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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