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

HRID 2197541ノート

反応式

HRID 2197541 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-627e866f29a844be9ace32299abed9da
出典データセット
uspto-grants-2012_12
特許番号
US08338604B2

反応ノート

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