Dimethylformamide → 2-(4-Fluoro-phenyl)-5-iodo-6-(methanesulfonyl-pent-4-enyl-amino)-furo[2,3-b]pyridine-3-carboxylic acid methylamide

HRID 2190173Notes

Reaction equation

HRID 2190173 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:22][C:11]3=[N:12][C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([I:16])[CH:15]=[C:10]3[C:9]=2[C:23]([NH:25][CH3:26])=[O:24])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:34][CH2:35][CH2:36][CH:37]=[CH2:38].CN(C=O)C>O>[CH3:26][NH:25][C:23]([C:9]1[C:10]2[C:11](=[N:12][C:13]([N:17]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:38][CH2:37][CH2:36][CH:35]=[CH2:34])=[C:14]([I:16])[CH:15]=2)[O:22][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 707041-Pentene, 5-bromo-HCID 580523242-(4-fluorophenyl)-5-iodo-N-methyl-6-(methylsulfonamido)furo[2,3-b]pyridine-3-carboxamide

Product 1

HCID 580523282-(4-Fluoro-phenyl)-5-iodo-6-(methanesulfonyl-pent-4-enyl-amino)-furo[2,3-b]pyridine-3-carboxylic acid methylamideYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(4-fluorophenyl)-5-iodo-N-methyl-6-(methylsulfonamido)furo[2,3-b]pyridine-3-carboxamide (440 mg), Cs2CO3 (322 mg, 1.1 eq.), 5-bromopent-1-ene (402 mg, 3 eq.) and dry DMF (4.5 ml) was stirred in a microwave reactor at 150° C. for 15 min and cooled to rt. Water was added and the mixture was extracted with methylene chloride. The organic layer was washed with 2× water. Silica gel flash chromatography using 0-11% ether-methylene chloride yielded the title compound (250 mg, 55%). MS (ESI) m/z 558.1 (M+1). Retention time=1.33 min (Method A).

Workup

  1. temperaturecooled to rt
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with 2× water

Sources & evidence

ORD record
ord-98dff851b12c432d8533cd24f9f5677f
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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