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Sodium hydride → N-(3,5-Difluoro-4-iodopyridin-2-yl)-N-((2-(trimethylsilyl)ethoxy)-methyl)propane-1-sulfonamide

HRID 710573
Notes
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Reaction equation

HRID 710573 reaction equation
[F:1][C:2]1[C:3]([NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12])=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[I:8].[H-].[Na+].[CH3:19][Si:20]([CH2:23][CH2:24][O:25][CH2:26]Cl)([CH3:22])[CH3:21]>CN(C=O)C>[F:1][C:2]1[C:3]([N:10]([CH2:26][O:25][CH2:24][CH2:23][Si:20]([CH3:22])([CH3:21])[CH3:19])[S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12])=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[I:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 86686187N-(3,5-Difluoro-4-iodopyridin-2-yl)propane-1-sulfonamide

Product 1

HCID 67365295N-(3,5-Difluoro-4-iodopyridin-2-yl)-N-((2-(trimethylsilyl)ethoxy)-methyl)propane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

To a solution of N-(3,5-difluoro-4-iodopyridin-2-yl)propane-1-sulfonamide (0.68 g, 1.88 mmol) in anhydrous DMF (25 ml) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.15 g, 3.8 mmol). The reaction mixture was stirred for 10 min, and then SEMCl (0.47 g, 2.8 mmol) was added. The mixture was stirred for 1 h and was then concentrated. Water was added and the mixture was extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate, and concentrated. The residue was chromatographed on silica gel (5 to 20% ethyl acetate in hexanes eluant) to provide the title compound. MS m/z 515.1 (M+Na).

Workup

  1. stirringThe mixture was stirred for 1 h
  2. concentrationwas then concentrated
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (5 to 20% ethyl acetate in hexanes eluant)

Sources & evidence

ORD record
ord-e5a70bf04cba4f2fbec9034ff4db4640
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181238B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes