4-Vinylpyridine → HCID 5327625、化合物

HRID 724921ノート

反応式

HRID 724921 の反応式
[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]

参加物

8

反応物 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 10547779HCID 10547779、化合物

生成物 1

HCID 5327625HCID 5327625、化合物収率 73.6%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8c8cc36736d548d3825fe289d5cd78a8
出典データセット
uspto-grants-1998_01
特許番号
US05705499

反応ノート

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