Sodium periodate → tert-butyl 5-oxo-3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 2175612노트

반응식

HRID 2175612 반응식
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[N:5][C:6]2[CH2:7][CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C:11]=2[CH:12]=1.I([O-])(=O)(=O)=[O:23].[Na+]>C(Cl)(Cl)(Cl)Cl.CC#N.O.C(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[O:23]=[C:10]1[N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:8][CH2:7][C:6]2[N:5]=[CH:4][C:3]([C:2]([F:20])([F:1])[F:21])=[CH:12][C:11]1=2

참가 물질

7

반응물 2

HCID 23667635Sodium periodateHCID 58885211tert-Butyl 3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

생성물 1

HCID 58562753tert-butyl 5-oxo-3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

시약·촉매·용매 4

HCID 6093376Ruthenium trichloride hydrate촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 18669661Acetonitrile tetrachloromethane용매

실험 절차

Into a 250 mL round-bottom flask, was placed a solution of tert-butyl 3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (as prepared in the previous step, 3.84 g, 0.01 mol, 1.00 equiv) in CCl4/CH3CN=10/1 (66 mL), a solution of sodium periodate (8.135 g, 38.01 mmol, 3.00 equiv) in water (20 mL) and Ruthenium(III)Chloride Hydrate (0.992 g, 0.30 equiv). The resulting solution was stirred for 12 h at room temperature, and then the mixture was diluted with 50 mL of CH2Cl2. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (1:50-1:10). The title compound was obtained as a white solid.

후처리

  1. customInto a 250 mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (1:50-1:10)

출처 및 근거

ORD 기록
ord-6ead46e23c774bfbbd4d14bbb962ff60
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062048B2

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