Water → tert-butyl 2-chloro-4-methyl-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 80825

반응식

HRID 80825 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[CH2:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:5][C:4]=2[N:3]=1.[OH2:20]>CCOC(C)=O.[Cl-].[Na+].O.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:8](=[O:20])[N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:5][C:4]=2[N:3]=1

참가 물질

6

반응물 2

HCID 962WaterHCID 86690273tert-butyl 2-chloro-4-methyl-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

생성물 1

HCID 86690274tert-butyl 2-chloro-4-methyl-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

시약·촉매·용매 3

HCID 61850Ruthenium trichloride촉매HCID 8857Ethyl Acetate용매2회HCID 57417360Sodium chloride; water용매

실험 절차

To a suspension of ruthenium trichloride (0.141 g, 0.681 mmol) and NaI04 (8.32 g, 38.9 mmol) in H2O (30 mL) at 0° C., a solution of tert-butyl 2-chloro-4-methyl-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (2.75 g, 9.73 mmol) in EtOAc (30 mL) was added. After stirring for 5 min., the reaction mixture was warmed up to rt and stirred. After stirring for 21.5 h, the mixture was diluted with EtOAc and brine. The organic layer was separated, dried over Na2SO4, filtered, and concentrated. The crude was purified by flash column chromatography on 80 g of silica gel (with 25 g pre-column of silica gel; eluent: heptane/EtOAc=100:0 to 70:30) to give tert-butyl 2-chloro-4-methyl-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (2.10 g) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.15 (s, 1H), 3.98 (t, J=6.32 Hz, 2 H), 3.13 (t, J=6.32 Hz, 2 H), 2.70 (s, 3 H), 1.58 (s, 9 H).

후처리

  1. stirringstirred
  2. stirringAfter stirring for 21.5 h
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by flash column chromatography on 80 g of silica gel (with 25 g pre-column of silica gel; eluent: heptane/EtOAc=100:0 to 70:30)

출처 및 근거

ORD 기록
ord-3d827cf773ca4ee4bb76c9575b7d598c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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