Diisopropylamine → 2-[4-(5-Bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol

HRID 734789ノート

反応式

HRID 734789 の反応式
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([O:7][CH2:8][CH2:9][OH:10])=[C:5]([CH3:13])[CH:4]=1)#[CH:2].Br[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1.C(NC(C)C)(C)C>C1COCC1.[Cu]I>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([C:2]#[C:1][C:3]2[CH:12]=[CH:11][C:6]([O:7][CH2:8][CH2:9][OH:10])=[C:5]([CH3:13])[CH:4]=2)=[N:16][CH:17]=1

参加物

6

反応物 3

HCID 7912DiisopropylamineHCID 693532,5-DibromopyridineHCID 575658612-(4-Ethynyl-2-methylphenoxy)ethanol

生成物 1

HCID 690586072-[4-(5-Bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

0.26 g (1.36 mmol) of CuI was added to a degassed solution of 11.98 g (68.00 mmol) of 2-(4-ethynyl-2-methylphenoxy)ethanol, 16.11 g (68.00 mmol) of 2,5-dibromopyridine, 0.96 g (1.36 mmol) of bis(triphenylphosphane)palladium (II) chloride, and 19.22 mL (136.00 mmol) of diisopropylamine in 500 mL of THF and the mixture was stirred for 4 hours at RT. The reaction mixture was evaporated down in vacuo and the residue taken up in 800 mL of EtOAc. The organic phase was with water and saturated aqueous NaCl solution washed, dried over sodium sulfate, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, gradient DCM/EtOAc 90:10→80:20). Yield: 13.20 g (58% of theoretical); C16H14BrNO2 (M=332.192); calc.: molpeak (M+H)+: 332/334 (Br); found: molpeak (M+H)+: 332/334 (Br); Rf value: 0.39 (silica gel, cyc/EtOAc 1:1).

後処理

  1. customThe reaction mixture was evaporated down in vacuo
  2. washwashed
  3. dry with materialdried over sodium sulfate
  4. customevaporated down in vacuo
  5. customThe crude product was purified by column chromatography (silica gel, gradient DCM/EtOAc 90:10→80:20)

出典と根拠

ORDレコード
ord-ea5cb6ad63444715a4a1454a4eed96ae
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

読み込み中…