Stannous Chloride → HCID 131732284, compound

HRID 2272322Notes

Reaction equation

HRID 2272322 reaction equation
[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:34]=[C:33]([F:35])[C:32]([N+:36]([O-])=O)=[C:31]([F:39])[CH:30]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.[Sn](Cl)Cl>CCOC(C)=O.C(O)C.O>[NH2:36][C:32]1[C:31]([F:39])=[CH:30][C:29]([N:24]([C:5]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:23][C:8]3[C:9]([C:19]([NH:21][CH3:22])=[O:20])=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[O:11][C:7]=3[CH:6]=2)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:34][C:33]=1[F:35]

Participants

6

Reactant 2

HCID 24479Stannous ChlorideHCID 131732283HCID 131732283, compound

Product 1

HCID 131732284HCID 131732284, compoundYield 55.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 5-cyclopropyl-6-(N-(3,5-difluoro-4-nitrophenyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (0.65 g, 1.16 mmol) and tin (II) chloride (0.66 g, 3.49 mmol) in EtOAc (10 mL) and ethanol (10 mL) was heated under reflux for 2 h. The reaction mixture was diluted with EtOAc and water and the suspension was filtered through celite. The organic layer was dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (0-50% EtOAc/hexanes) to afford the title compound (0.34 g, 55%) as a white solid. LCMS (m/z, ES+)=530.2 (M+H+).

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationthe suspension was filtered through celite
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a76b00bb440d47409a4039c66d16a454
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

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