4-Vinylpyridine → HCID 5327625, 화합물

HRID 724921노트

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HRID 724921 반응식
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](I)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2].[CH:21]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)=[CH2:22].C(N(CC)CC)C.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>CN(C)C=O.O.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>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](/[CH:22]=[CH:21]/[C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2]

참가 물질

8

반응물 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 10547779HCID 10547779, 화합물

생성물 1

HCID 5327625HCID 5327625, 화합물수율 73.6%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
125 °C

실험 절차

A mixture containing 5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]-diazepin-6-one (0.7 g, 1.9 mmol), 4-vinylpyridine (0.3 mL, 2.9 mmol), bis(triphenylphosphine)palladium(II) chloride (60 mg, 0.09 mmol), triethylamine (1.8 mL, 12.8 mmol), and 1 crystal of 2,6-di-tert-butyl-4-methylphenol in 4 mL of N,N-dimethylformamide was heated at 125° C. under argon for 3 hours. The reaction mixture was then cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (magnesium sulfate), and concentrated to give a yellow oil. Purification by flash chromatography, eluting with ethyl acetate/hexanes, and recrystallization (ethyl acetate/hexanes) provided the 0.5 g of the title compound as yellow crystals, m.p. 150° C.

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by flash chromatography
  8. washeluting with ethyl acetate/hexanes, and recrystallization (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-8c8cc36736d548d3825fe289d5cd78a8
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705499

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