Potassium Fluoride → (Z)-6-(2-ethoxyvinyl)-8-phenyl-[1,2,4]triazolo[4,3-a]pyridine

HRID 1958465ノート

反応式

HRID 1958465 の反応式
Br[C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)/[CH:22]=[CH:23]\[O:24][CH2:25][CH3:26])CCC.[F-].[K+]>[Cl-].C([N+](CC)(CC)CC)C.CN(C=O)C.O.C(OCC)(=O)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>[CH2:25]([O:24]/[CH:23]=[CH:22]\[C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1)[CH3:26]

参加物

9

反応物 3

HCID 522689Potassium FluorideHCID 5706773cis-1-Ethoxy-2-(tri-n-butylstannyl)ethyleneHCID 582079196-Bromo-8-phenyl-[1,2,4]triazolo[4,3-a]pyridine

生成物 1

HCID 58207976(Z)-6-(2-ethoxyvinyl)-8-phenyl-[1,2,4]triazolo[4,3-a]pyridine収率 52%

試薬・触媒・溶媒 5

HCID 5946Tetraethylammonium Chloride触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-bromo-8-phenyl-[1,2,4]triazolo[4,3-a]pyridine (26.1 mg, 0.095 mmol), (Z)-tributyl(2-ethoxyvinyl)stannane (34.6 mg, 0.095 mmol) and tetraethylammonium chloride (16 mg, 0.095 mmol) in DMF (0.5 mL) was added PdCl2(PPh3)2 (2 mg, 0.005 mmol). The reaction was heated at 80° C. overnight, cooled to rt, added an aqueous of KF (1.1 eq) in water (95 μL) and further stirred for 30 mins, then diluted with ethyl acetate (2 mL), filtered and rinsed with ethyl acetate (8 mL). The mixture was then washed with water (2×2 mL), separated, dried and concentrated. The residue was purified by a flash column using a gradient of ethyl acetate in hexane (50-75%) as an eluent to give compound (13 mg, 52% yield).

後処理

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. washrinsed with ethyl acetate (8 mL)
  4. washThe mixture was then washed with water (2×2 mL)
  5. customseparated
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by a flash column

出典と根拠

ORDレコード
ord-93fc5b595b874669bbebb92571bcde7b
出典データセット
uspto-grants-2013_04
特許番号
US08410128B2

反応ノート

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