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

HRID 1852193Notes

Reaction equation

HRID 1852193 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-acdc7310be3c4de389397427d46c0e0e
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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