4-Methoxybenzenesulfonyl chloride → HCID 51355175、化合物

HRID 1052473ノート

反応式

HRID 1052473 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:28]([C:25]2[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=2)(=[O:30])=[O:29])[C:5]([Cl:8])=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 218583543-Amino-5-bromo-2-chloropyridine

生成物 1

HCID 51355175HCID 51355175、化合物収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-Bromo-2-chloropyridin-3-amine (1 g, 4.82 mmol) was dissolved in THF (5.5 ml) and a solution of sodium bis(trimethylsilyl)amide (1M in THF, 14.5 ml, 14.5 mmol) was added dropwise. Ten minutes later, 4-methoxybenzene-1-sulfonyl chloride (3 g, 14.5 mmol) was added and the reaction mixture stirred for 2 h. A saturated solution of sodium bicarbonate was then added dropwise and the reaction mixture extracted with dichloromethane (×3). The organic phase was dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. The resulting crude was purified by flash chromatography using SP1® Purification System (0% to 10%, dichloromethane-ethyl acetate) to obtain 1.49 g (82% yield) of the title compound. Purity: 100%

後処理

  1. extractionthe reaction mixture extracted with dichloromethane (×3)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customThe resulting crude was purified by flash chromatography
  6. customSP1® Purification System (0% to 10%, dichloromethane-ethyl acetate)

出典と根拠

ORDレコード
ord-26c148f96d4e476a8789d446470d163f
出典データセット
uspto-grants-2016_07
特許番号
US09388189B2

反応ノート

読み込み中…