Potassium Carbonate → 7-chloro-3-(3,5-dimethoxyphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one

HRID 524052

반응식

HRID 524052 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([NH:10][CH3:11])[C:5]([CH:6]=O)=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][C:23](OC)=[O:24])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]2[C:5]([CH:6]=[C:22]([C:16]3[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:14]([O:13][CH3:12])[CH:15]=3)[C:23](=[O:24])[N:10]2[CH3:11])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 592191Methyl 3,5-dimethoxyphenylacetateHCID 234345716-Chloro-4-(methylamino)nicotinaldehyde

생성물 1

HCID 867135767-chloro-3-(3,5-dimethoxyphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one수율 80.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
105 °C

실험 절차

A mixture of 6-chloro-4-(methylamino)nicotinaldehyde (3.7 g, 21.7 mmol), methyl 2-(3,5-dimethoxyphenyl)acetate (4.5 g, 21.7 mmol) and potassium carbonate (9.0 g, 65.1 mmol) in N,N-dimethylformamide (30 mL) was heated at 105° C. for 5 h. LCMS showed the reaction was completed. The reaction was cooled to RT, quenched with water (200 mL), and filtered. The filtration cake was washed by petroleum ether (50 mL) and ethyl acetate (50 mL) to afford the title compound (5.8 g, 77%) as a yellow solid. MS (ES+) C18H19ClN2O3 requires: 346, 348. found: 347, 349 [M+H]+.

후처리

  1. temperatureThe reaction was cooled to RT
  2. customquenched with water (200 mL)
  3. filtrationfiltered
  4. washThe filtration cake was washed by petroleum ether (50 mL) and ethyl acetate (50 mL)

출처 및 근거

ORD 기록
ord-9cf9ea22fa634854a14f4dd1149174fa
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340514B2

연결된 노트

불러오는 중…