m-Chloroperbenzoic acid → 3-Methanesulfonyl-5-phenylethynylpyridine

HRID 606905

反応式

HRID 606905 の反応式
Cl[C:2]1C=C(C(OO)=O)C=CC=1.CS[C:14]1[CH:15]=[N:16][CH:17]=[C:18]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1.[S:28]([O-:31])([O-:30])=S.[Na+].[Na+]>ClCCl>[CH3:2][S:28]([C:14]1[CH:15]=[N:16][CH:17]=[C:18]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1)(=[O:31])=[O:30]

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 15847209sodium thiosulfite anhydrousHCID 670478293-Methylsulfanyl-5-phenylethynylpyridine

生成物 1

HCID 670474593-Methanesulfonyl-5-phenylethynylpyridine収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Add 3-chlorobenzenecarboperoxoic acid (79.2 mg, 0.46 mmol) to a solution of 3-methylsulfanyl-5-phenylethynyl-pyridine, (prepared as described in EXAMPLE 128), (34.4 mg, 0.15 mmol) in dichloromethane (1 mL) at 0° C., warm to room temperature and stir for 2 h. Dilute with a 5% aqueous solution of sodium thiosulfite and dichloromethane. After separating the layers, sequentially wash the organic layer with a 5% aqueous solution of sodium thiosulfite and an aqueous saturated solution of sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 100:0 to 100:50 hexanes:ethyl acetate, to give the title compound (24.8 mg, 64%).

後処理

  1. customAfter separating the layers
  2. washsequentially wash the organic layer with a 5% aqueous solution of sodium thiosulfite
  3. dry with materialan aqueous saturated solution of sodium chloride, dry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 100:0 to 100:50 hexanes

出典と根拠

ORDレコード
ord-2aba3d60f40440ab85220b3af4fb4b61
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

関連ノート

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