Potassium Carbonate → Ethyl 5-(4-chloro-3-methyl-[1,8]-naphthyridin-2-yl)pentanoate

HRID 2187379

반응식

HRID 2187379 반응식
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].B1C2CCCC1CCC2.C([O-])([O-])=O.[K+].[K+].Cl[C:26]1[C:35]([CH3:36])=[C:34]([Cl:37])[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CN(C=O)C>[Cl:37][C:34]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[C:26]([CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])[C:35]=1[CH3:36]

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 74786Ethyl 4-pentenoateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 220826612,4-Dichloro-3-methyl-1,8-naphthyridine

생성물 1

HCID 18475432Ethyl 5-(4-chloro-3-methyl-[1,8]-naphthyridin-2-yl)pentanoate

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

To a solution of ethyl 4-pentenoate (2.5 g, 20 mmol) in 60 mL THF was added 9-BBN (0.5 M in THF, 47 mL, 23 mmol) gradually at room temperature. After stirring for 10 hours, it was treated with Pd(OAc)2 (0.4 g, 2.0 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (DPPF) (1.1 g, 2.0 mmol), K2CO3 (powder, 8.1 g, 58 mmol), 2,4-dichloro-3-methyl-naphthyridine (L) (3.6 g, 20 mmol) and 50 mL DMF. The reaction mixture was purged with argon for 5 minutes and then refluxed at 75° C. for 24 hours. It was cooled to room temperature and treated with 10 mL ethanolamine and stirred for 30 minutes. The mixture was diluted with 400 mL H2O and extracted with EtOAc(×3). The combined organic layers were washed with brine and dried. After solvent removal, the residue was purified by silica gel chromatography using EtOAc/hexanes (1:1) to give the desired product 3-3 as a liquid.

후처리

  1. customThe reaction mixture was purged with argon for 5 minutes
  2. temperatureIt was cooled to room temperature
  3. additiontreated with 10 mL ethanolamine
  4. stirringstirred for 30 minutes
  5. additionThe mixture was diluted with 400 mL H2O
  6. extractionextracted with EtOAc(×3)
  7. washThe combined organic layers were washed with brine
  8. customdried
  9. customAfter solvent removal
  10. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-f61ba7ed573a42e384bb8cb7db67a911
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06410526B1

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