Tributylvinyltin → 6-methoxy-1-methyl-7-vinyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

HRID 1244057노트

반응식

HRID 1244057 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[N:4][C:3]=1[O:14][CH3:15].[CH2:16]([Sn](CCCC)(CCCC)C=C)[CH2:17]CC>O1CCOCC1.O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[CH3:15][O:14][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH:16]=[CH2:17])[N:9]([CH3:12])[C:8](=[O:13])[CH2:7][CH2:6]2

참가 물질

7

반응물 2

HCID 81998TributylvinyltinHCID 219318227-bromo-6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

생성물 1

HCID 219317566-methoxy-1-methyl-7-vinyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one수율 36.7%

시약·촉매·용매 4

HCID 13169693Triphenylphosphine palladium dichloride촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A mixture of 690 mg (2.5 mmol) of 7-bromo-6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one, 0.8 ml (2.7 mmol) of tri-n-butyl-vinyltin and 100 mg of bis(triphenylphosphine-palladium(II) chloride in 20 ml of dioxane was heated under nitrogen to 100° C. for 6 hours. The reaction mixture was cooled to room temperature and diluted with water and ethyl acetate. The ethyl acetate solution was washed with water several times. To this ethyl acetate solution was added 1 ml of saturated KF, and the mixture filtered. The filtrate was dried, evaporated, and the residue chromatographed on silica using 1 5 ethyl acetate/hexanes as the elutant. Appropriate fractions were combined and evaporated to afford 200 mg of 6-methoxy-1-methyl-7-vinyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one. 1H NMR (CDCl3) δ 7.28 (s, 1H), 6.90 (d,d 1H), 5.75 (d, 1H), 5.35 (d, 1H), 3.95 (s, 3H), 3.26 (s, 3H), 3.0 (m, 2H), 2.7 (m, 2H) Mass spectrum: m/e=219.3 (p+1).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe ethyl acetate solution was washed with water several times
  3. additionTo this ethyl acetate solution was added 1 ml of saturated KF
  4. filtrationthe mixture filtered
  5. customThe filtrate was dried
  6. customevaporated
  7. customthe residue chromatographed on silica using 1 5 ethyl acetate/hexanes as the elutant
  8. customevaporated

출처 및 근거

ORD 기록
ord-f0dc5f7502754a6cb5e5a63540cd4006
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119207B2

반응 노트

불러오는 중…