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

HRID 1748377ノート

反応式

HRID 1748377 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 498840Bis(benzonitrile)palladium chloride触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 702Ethanol溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-875b7782490143b2bb26d7ade1c32cc2
出典データセット
uspto-grants-2015_10
特許番号
US09150572B2

反応ノート

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