Diisopropylamine → 5-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

HRID 1916530

반응식

HRID 1916530 반응식
[CH2:1]([C:5]1[CH:16]=[CH:15][C:8]([CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)[CH2:2][C:3]#[CH:4].Br[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=1.C(NC(C)C)(C)C>C1COCC1.O.[Cu]I>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:4]#[C:3][CH2:2][CH2:1][C:5]2[CH:16]=[CH:15][C:8]([CH2:9][N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=2)=[N:19][CH:20]=1

참가 물질

7

반응물 3

HCID 7912DiisopropylamineHCID 693532,5-DibromopyridineHCID 859698431-(4-But-3-ynyl-benzyl)-pyrrolidine

생성물 1

HCID 690713915-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

A mixture of 200 mg (0.94 mmol) 1-(4-but-3-ynyl-benzyl)-pyrrolidine, 222 mg (0.94 mmol) 2,5-dibromopyridine, 13.2 mg (0.02 mmol) tetrakis-triphenylphosphane-palladium, 3.6 mg (0.02 mmol) CuI and 0.27 mL diisopropylamine in 10 mL THF is heated for 4 h at 40° C. under an argon atmosphere. The reaction mixture is diluted with water, exhaustively extracted with EtOAc, the organic phase is washed with 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 95:5:0.5).

후처리

  1. extractionexhaustively extracted with EtOAc
  2. washthe organic phase is washed with saturated, aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

출처 및 근거

ORD 기록
ord-e13c917bb04b4f3c8bd29402a92662eb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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