Dimethylformamide → Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate

HRID 55778노트

반응식

HRID 55778 반응식
Cl[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].CN(C=O)C>O.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.Cl[Pd]Cl.[Fe+2]>[CH3:14][O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:22]1[CH:23]=[CH:24][C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:20][CH:21]=1)[C:11]([CH3:12])=[CH:10]2

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 27343694-Methoxycarbonylphenylboronic acidHCID 49146642-Chloro-6-methoxy-3-methylquinoline

생성물 1

HCID 66980055Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate수율 25%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, 0.482 mmol), 4-(methoxycarbonyl)phenylboronic acid (184 mg, 1.02 mmol), TEA (0.35 mL, 2.41 mmol), and PdCl2(dppf) (35 mg, 0.048 mmol) was added 2 mL of DMF under argon. The mixture was then stirred for 2.5 h at 120° C. in a microwave reactor. The crude mixture was then diluted with water (25 mL) and extracted with EtOAc (25 mL×2). The organics were washed with brine (50 mL), dried over sodium sulfate, and concentrated to yield 250 mg of crude material. The crude was purified via column chromatography with a gradient of 5% EtOAc in hexanes to 80% EtOAc in hexanes to yield 37 mg (25% yield) of methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate.

후처리

  1. extractionextracted with EtOAc (25 mL×2)
  2. washThe organics were washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto yield 250 mg of crude material
  6. customThe crude was purified via column chromatography with a gradient of 5% EtOAc in hexanes to 80% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-566c6ba9444145aa914b4bae42d128ca
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433618B2

반응 노트

불러오는 중…