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

HRID 2175612ノート

反応式

HRID 2175612 の反応式
[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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6093376Ruthenium trichloride hydrate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 18669661Acetonitrile tetrachloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6ead46e23c774bfbbd4d14bbb962ff60
出典データセット
uspto-grants-2015_06
特許番号
US09062048B2

反応ノート

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