Propargyl alcohol → N-[3-(3-hydroxyprop-1-yn-1-yl)pyrazin-2-yl]-2-(trifluoromethyl)benzenesulfonamide

HRID 2401031ノート

反応式

HRID 2401031 の反応式
Cl[C:2]1[C:3]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:22]([OH:25])[C:23]#[CH:24].CC(O[K])=O>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:25][CH2:22][C:23]#[C:24][C:2]1[C:3]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1

参加物

7

反応物 3

HCID 7859Propargyl alcoholHCID 57586069N-(3-chloropyrazin-2-yl)-2-(trifluoromethyl)benzenesulfonamideHCID 178476685HCID 178476685、化合物

生成物 1

HCID 57444251N-[3-(3-hydroxyprop-1-yn-1-yl)pyrazin-2-yl]-2-(trifluoromethyl)benzenesulfonamide収率 50%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

N-(3-chloropyrazin-2-yl)-2-(trifluoromethyl)benzenesulfonamide (1.35 g; 4.0 mmol; 1.00 eq.) and 2-propyn-1-ol (336 mg 6.0 mmol; 1.5 eq.) were dissolved in 10 mL of DMF under nitrogen atmosphere. To the reaction mixture was added CH3COOK (588 mg; 6.0 mmol; 1.5 eq.) CuI (40 mg; 0.2 mmol; 0.05 eq.) and Pd(PPh3)2Cl2 (28 mg; 0.04 mmol) under nitrogen. The reaction mixture was then heated at 100° C. under nitrogen for 2 hours. After removal of the solvent by distillation in vacuo, the residue was triturated with water (40 mL) and extracted with diethyl ether (3×30 mL). The organic layer was dried over MgSO4 and evaporated down. The crude product was purified by silica gel column chromatography using a mixture of hexane and AcOEt to give pure N-[3-(3-hydroxyprop-1-yn-1-yl)pyrazin-2-yl]-2-(trifluoromethyl)benzenesulfonamide as a yellowish solid (702 mg, 50% yield, 98% HPLC purity).

後処理

  1. customAfter removal of the solvent
  2. distillationby distillation in vacuo
  3. customthe residue was triturated with water (40 mL)
  4. extractionextracted with diethyl ether (3×30 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated down
  7. customThe crude product was purified by silica gel column chromatography
  8. additiona mixture of hexane and AcOEt

出典と根拠

ORDレコード
ord-375084f141a54e6a90c69d261898da8e
出典データセット
uspto-grants-2014_08
特許番号
US08796280B2

反応ノート

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