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

HRID 1472633노트

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HRID 1472633 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

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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-01a2a0f3e5464ebeb9f40d96779a618c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012646B2

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