2-Bromo-5-nitropyridine → 1,2,3,6-Tetrahydro-1-[4-(5-nitro-2-pyridinyl)-3-butynyl]-4-phenylpyridine

HRID 53642

반응식

HRID 53642 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]1([C:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][C:25]#[CH:26])[CH2:21][CH:22]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>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:20]2[CH2:19][CH:18]=[C:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:22][CH2:21]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

참가 물질

6

반응물 2

HCID 782402-Bromo-5-nitropyridineHCID 107985574-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butyne

생성물 1

HCID 106880901,2,3,6-Tetrahydro-1-[4-(5-nitro-2-pyridinyl)-3-butynyl]-4-phenylpyridine

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

A solution of 2-bromo-5-nitropyridine (4.23 g, 0.02 mol) and the alkyne prepared in Step (a) (4.0 g, 0.019 mol) in 7.9 mL of triethylamine and 100 mL of acetonitrile is degassed by bubbling in dry nitrogen for 15 minutes, and 0.27 g (0.0004 mol) of bis(triphenylphosphine)palladium chloride and 0.07 g (0.0004 mol) of cuprous iodide are added. The flask is flushed with nitrogen and the mixture is stirred at room temperature for 6 hours. The solvent is removed under reduced pressure and the residue is partitioned between 100 mL of dichloromethane and 100 mL of saturated aqueous sodium bicarbonate. The aqueous layer is extracted with 50 mL of dichloromethane and the combined organic layers are washed with 50 mL of 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, containing 0.3 mol of water; mp 133°-134° 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 100 mL of dichloromethane and 100 mL of saturated aqueous sodium bicarbonate
  5. extractionThe aqueous layer is extracted with 50 mL of dichloromethane
  6. washthe combined organic layers are washed with 50 mL of 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-50743b3e0db3497584f798ee4c016561
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620988

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