Diisopropylamine → 5-Bromo-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

HRID 1916523ノート

反応式

HRID 1916523 の反応式
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([O:7][CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1)#[CH:2].Br[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=1.C(NC(C)C)(C)C>C1COCC1.Cl[Cu]>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:2]#[C:1][C:3]2[CH:16]=[CH:15][C:6]([O:7][CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)=[CH:5][CH:4]=2)=[N:19][CH:20]=1

参加物

6

反応物 3

HCID 7912DiisopropylamineHCID 693532,5-DibromopyridineHCID 859698151-[2-(4-Ethynyl-phenoxy)-ethyl]-pyrrolidine

生成物 1

HCID 673653025-Bromo-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

A mixture of 9.6 g (44.6 mmol) 1-[2-(4-ethynyl-phenoxy)-ethyl]-pyrrolidine, 10.6 g (44.6 mmol) 2,5-dibromopyridine, 626 mg (0.9 mmol) tetrakis-triphenylphosphane-palladium, 170 mg (0.9 mmol) CuCl and 12.6 mL diisopropylamine in 500 mL THF is heated for 3 h at 40° C. under an argon atmosphere. The solvent is distilled off i.vac., the residue is taken up in EtOAc, the organic phase is washed with water and saturated, aqueous NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 90:10:1).

後処理

  1. distillationThe solvent is distilled off i.vac
  2. washthe organic phase is washed with water
  3. dry with materialsaturated, aqueous NaCl solution and dried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH/NH3 90:10:1)

出典と根拠

ORDレコード
ord-6188a537918f4206819aed36378be6c4
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

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