4-Fluorobenzenesulfonyl chloride → N-(5-chloro-3-methylpyridin-2-yl)-4-fluorobenzenesulfonamide

HRID 594115

反応式

HRID 594115 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([NH:8][S:17]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 3502322-Amino-5-chloro-3-methylpyridine

生成物 1

HCID 89876053N-(5-chloro-3-methylpyridin-2-yl)-4-fluorobenzenesulfonamide収率 47.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

反応条件

温度
20 °C

実験手順

To a solution of 5-chloro-3-methylpyridin-2-amine (500 mg, 3.51 mmol) in pyridine (7 mL) stirred in air at room temperature was added a solution of 4-fluorobenzene-1-sulfonyl chloride (819 mg, 4.21 mmol) in pyridine (7 mL). The reaction mixture was stirred at 20° C. for 16 hours then the solvent was evaporated in vacuo. The crude was passed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with methanol followed by 2M ammonia/methanol, then a sulphonic acid (SCX) SPE cartridge eluting with methanol followed by 2M ammonia/methanol. The appropriate fractions were combined and evaporated under a stream of nitrogen to give the crude product. The crude was purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane+0-20% methanol gradient). The appropriate fractions were combined and evaporated in vacuo to give the title compound (502 mg) as an off-white solid. LCMS (2 min, formic) Rt 1.02 min, m/z (ES+) 301 (M+H).

後処理

  1. customthe solvent was evaporated in vacuo
  2. extractionThe crude was passed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge
  3. washeluting with methanol
  4. washa sulphonic acid (SCX) SPE cartridge eluting with methanol
  5. customevaporated under a stream of nitrogen
  6. customto give the crude product
  7. customThe crude was purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane+0-20% methanol gradient)
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-1b28b376a0944a7cb6660adc1d8ac78f
出典データセット
uspto-grants-2016_01
特許番号
US09242972B2

関連ノート

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