Triethylamine → Ethyl 7-hydroxy-1,5-naphthyridine-3-carboxylate

HRID 513927노트

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HRID 513927 반응식
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1)C1C=CC=CC=1.C(OC1C=NC2C(C=1)=NC=C(Br)C=2)C1C=CC=CC=1.CCN(CC)CC>CCO.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 904173103-(Benzyloxy)-7-bromo-1,5-naphthyridineHCID 90417541Ethyl 7-(benzyloxy)-1,5-naphthyridine-3-carboxylate

생성물 1

HCID 136227102Ethyl 7-hydroxy-1,5-naphthyridine-3-carboxylate수율 67%

시약·촉매·용매 3

HCID 498840Bis(benzonitrile)palladium chloride촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 702Ethanol용매

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온도
140 °C

실험 절차

Ethyl 7-(benzyloxy)-1,5-naphthyridine-3-carboxylate. A mixture of 3-(benzyloxy)-7-bromo-1,5-naphthyridine (30.0 g, 95.5 mmol), Et3N (19.47 g, 193 mmol), Pd(PhCN)2Cl2 (1.2 g, 3.13 mmol) and dppf (5.28 g, 9.5 mmol) in EtOH (500 mL) was pressurized to 15 bars with CO gas. Then the mixture was heated at 140° C. for 24 h. After cooling to ambient temperature, the solvent was removed under reduced pressure. Purification (FCC, SiO2, DCM/EtOAc, 1:1) afforded the title compound as a yellow solid (14 g, 67%). [M+H]=309.3.

후처리

  1. temperatureAfter cooling to ambient temperature
  2. customthe solvent was removed under reduced pressure
  3. customPurification (FCC, SiO2, DCM/EtOAc, 1:1)

출처 및 근거

ORD 기록
ord-ead6abf89fb24054913bcae122344102
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102674B2

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