Water → Ethyl 1-(2-bromobenzyl)-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate

HRID 1497695노트

반응식

HRID 1497695 반응식
C[N:2]([CH3:19])/[CH:3]=[C:4](/[C:10](=[O:18])[C:11]1[C:16](Cl)=[CH:15][CH:14]=[CH:13][N:12]=1)\[C:5]([O:7][CH2:8][CH3:9])=[O:6].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1CN.O>CC(N(C)C)=O>[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:19][N:2]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:18])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3]1

참가 물질

6

반응물 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 3340722-BromobenzylamineHCID 86725448(Z)-Ethyl 3-(dimethylamino)-2-(3-chloropicolinoyl)acrylate

생성물 1

HCID 86725447Ethyl 1-(2-bromobenzyl)-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate수율 49.2%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
74 °C

실험 절차

To a brown solution of (Z)-ethyl 2-(3-chloropicolinoyl)-3-(dimethylamino)acrylate (35) (850 mg, 3.01 mmol) in DMA (dimethylacetamide) (50 mL) were added a solid powder of tribasic potassium phosphate (1.4 g, 6.61 mmol) and then (2-bromophenyl)methanamine (615 mg, 3.31 mmol) at room temperature under a nitrogen atmosphere. The resulting brown suspension was heated to 74° C. and stirred for 15 h at which time LCMS analysis indicated the absence of starting material. Then, it was cooled to room temperature and poured slowly into water (100 mL). Then, the organic compound was extracted into dichloromethane (2×200 mL). The combined extracts were washed with water, brine solution, and dried over anhydrous MgSO4. Filtration and concentration gave a crude brown oil which was purified using an ISCO (120 g) column, eluting with ethyl acetate in hexanes (0 to 100%) and then 5 to 10% methanol in dichloromethane. The pure fractions were combined and the solvent was removed under vacuum to obtain ethyl 1-(2-bromobenzyl)-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate (36) (574 mg, 46.8% yield) as a light brown solid.

후처리

  1. customat room temperature
  2. temperatureThen, it was cooled to room temperature
  3. extractionThen, the organic compound was extracted into dichloromethane (2×200 mL)
  4. washThe combined extracts were washed with water, brine solution
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationFiltration and concentration
  7. customgave a crude brown oil which
  8. customwas purified
  9. washeluting with ethyl acetate in hexanes (0 to 100%)
  10. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-c0a639510e264721a925bc287ab81fff
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199987B2

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