2-Bromo-5-nitropyridine → 1-[4-(5-Nitro-2-pyridinyl)-3-butynyl]-4-(2-pyridinyl)piperazine

HRID 326552노트

반응식

HRID 326552 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.N1C=CC=CC=1[CH:17]1[CH2:22][NH:21][CH2:20][CH2:19][N:18]1[CH2:23][CH2:24][C:25]#[CH:26]>C(N(CC)CC)C.C(#N)C.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>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:26]#[C:25][CH2:24][CH2:23][N:18]2[CH2:17][CH2:22][N:21]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:20][CH2:19]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

참가 물질

6

반응물 2

HCID 782402-Bromo-5-nitropyridineHCID 197352474-[(2-Pyridyl)-1-piperazinyl]-1-butyne

생성물 1

HCID 197352531-[4-(5-Nitro-2-pyridinyl)-3-butynyl]-4-(2-pyridinyl)piperazine

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

A solution of 2-bromo-5-nitropyridine (3.11 g, 0.015 mol) and the alkyne prepared in Step (a) (3.0 g, 0.014 mol) in 5.8 mL of triethylamine and 60 mL of acetonitrile is degassed by bubbling in dry nitrogen for 15 minutes, and 0.2 g (0.0003 mol) of bis(triphenylphosphine)palladium chloride and 0.05 g (0.0003 mol) of cuprous iodide are added. The flask is flushed with nitrogen and the mixture is stirred at room temperature for 5 hours. The solvent is removed under reduced pressure, and the residue is partitioned between 50 mL of dichloromethane and 50 mL of saturated aqueous sodium bicarbonate. The aqueous layer is extracted with 30 mL of dichloromethane and the combined organic layers are washed with water and dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 1% methanol/ 99% dichloromethane) to give the title compound as a brown solid; mp 126°-126.5° C.

후처리

  1. customby bubbling in dry nitrogen for 15 minutes
  2. customThe flask is flushed with nitrogen
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is partitioned between 50 mL of dichloromethane and 50 mL of saturated aqueous sodium bicarbonate
  5. extractionThe aqueous layer is extracted with 30 mL of dichloromethane
  6. washthe combined organic layers are washed with water
  7. dry with materialdried (sodium sulfate)
  8. customthe solvent is removed in vacuo
  9. customThe residue is chromatographed (silica gel, 1% methanol/ 99% dichloromethane)

출처 및 근거

ORD 기록
ord-7d349aa6bc35420aa0c2554879d603ad
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270312

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