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

HRID 710573
ノート
印刷プレビュー

反応式

HRID 710573 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e5a70bf04cba4f2fbec9034ff4db4640
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181238B2

反応ノート

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