Cesium carbonate → 6-({2-[Allyl-(2-nitro-benzenesulfonyl)-amino]-ethyl}-methanesulfonyl-amino)-2-(4-fluoro-phenyl)-5-iodo-furo[2,3-b]pyridine-3-carboxylic acid methylamide

HRID 2190182Notes

Reaction equation

HRID 2190182 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].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:33]([N:36]([CH2:49][CH2:50]Br)[S:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[N+:46]([O-:48])=[O:47])(=[O:39])=[O:38])[CH:34]=[CH2:35]>CC(N(C)C)=O>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:15]([CH2:50][CH2:49][N:36]([CH2:33][CH:34]=[CH2:35])[S:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[N+:46]([O-:48])=[O:47])(=[O:38])=[O:39])[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]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 580523242-(4-fluorophenyl)-5-iodo-N-methyl-6-(methylsulfonamido)furo[2,3-b]pyridine-3-carboxamideHCID 58052488N-Allyl-N-(2-bromo-ethyl)-2-nitro-benzenesulfonamide

Product 1

HCID 666637406-({2-[Allyl-(2-nitro-benzenesulfonyl)-amino]-ethyl}-methanesulfonyl-amino)-2-(4-fluoro-phenyl)-5-iodo-furo[2,3-b]pyridine-3-carboxylic acid methylamideYield 19.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-(4-Fluoro-phenyl)-5-iodo-6-methanesulfonylamino-furo[2,3-b]pyridine-3-carboxylic acid methylamide (150 mg, 0.31 mmol) is dissolved in DMA (4 mL) and Cs2CO3 (110 mg, 0.34 mmol) and N-Allyl-N-(2-bromo-ethyl)-2-nitro-benzenesulfonamide (214 mg, 0.61 mmol) is added and the mixture is placed in the microwave for 30 min at 150° C. The mixture is then filtered and the solid is washed with EtOAc (30 mL). The organic is washed with H2O (10 mL) then Brine (20 mL) and then dried over Na2SO4 then concentrated to dryness. HPLC (CH3CN/H2O/0.1% TFA) provides 6-({2-[Allyl-(2-nitro-benzenesulfonyl)-amino]-ethyl}-methanesulfonyl-amino)-2-(4-fluoro-phenyl)-5-iodo-furo[2,3-b]pyridine-3-carboxylic acid methylamide (45 mg, 19%). MS-ES [M+H]+=758.3.

Workup

  1. filtrationThe mixture is then filtered
  2. washthe solid is washed with EtOAc (30 mL)
  3. washThe organic is washed with H2O (10 mL)
  4. dry with materialBrine (20 mL) and then dried over Na2SO4
  5. concentrationthen concentrated to dryness

Sources & evidence

ORD record
ord-c5eeb12a48894b3db8ac01a8401a8a13
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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