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

HRID 1916523노트

반응식

HRID 1916523 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6188a537918f4206819aed36378be6c4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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