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

HRID 1244057ノート

反応式

HRID 1244057 の反応式
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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 13169693Triphenylphosphine palladium dichloride触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f0dc5f7502754a6cb5e5a63540cd4006
出典データセット
uspto-grants-2006_10
特許番号
US07119207B2

反応ノート

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