Potassium Carbonate → 4-Chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline

HRID 1852193노트

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HRID 1852193 반응식
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.[CH:15]([O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH:15]([CH3:17])[CH3:16])=[CH:20][CH:21]=2)[CH:11]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 36987264-Isopropoxybenzeneboronic acidHCID 228320542,4-Dichloro-7-methoxyquinoline

생성물 1

HCID 709782674-Chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline수율 85.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

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온도
90 °C

실험 절차

To a degassed solution of 2,4-dichloro-7-methoxyquinoline (1 g, 4.3 mmol) in dioxane/water (8:2) was added 4-isopropoxyphenylboronic acid (870 mg, 4.82 mmol) followed by potassium carbonate (1.2 g, 8.7 mmol) and Pd(PPh3)4 (253 mg, 0.22 mmol) at room temperature under nitrogen atmosphere. The reaction mass was heated at 90° C. for 18 h. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to afford 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline (1.2 g, 85%) as off white solid. MS: MS m/z 328.7 (M++1).

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  5. customevaporated under reduced pressure
  6. customto get crude compound
  7. customThe crude compound was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-acdc7310be3c4de389397427d46c0e0e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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