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

HRID 2197541노트

반응식

HRID 2197541 반응식
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]

참가 물질

9

반응물 3

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

생성물 1

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

시약·촉매·용매 5

HCID 5946Tetraethylammonium Chloride촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-627e866f29a844be9ace32299abed9da
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338604B2

반응 노트

불러오는 중…