Potassium Carbonate → HCID 70978460, compound

HRID 1852281Notes

Reaction equation

HRID 1852281 reaction equation
Cl[N: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)[CH2:3]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>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[CH2:3][N: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 86683275HCID 86683275, compound

Product 1

HCID 70978460HCID 70978460, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,4-dichloro-7-methoxyisoquinolin (0.7 g, 3.07 mmol), 4-isopropoxyphenylboronic acid (0.60 g, 3.38 mmol) in 1,4-Dioxane (15 ml) and water (10 ml) was added K2CO3 (0.84 g, 6.14 mmol). The reaction mass was degasified for 20 min. Pd (Ph3P)4 (0.17 g, 0.15 mmol) was added to the above reaction mass and degasified again for 5 min at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 90° C. for 18 h. The reaction mass was evaporated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (0.85 g, 84%) as white solid. 1HNMR (400 MHz, CDCl3): δ ppm 8.25-8.22 (d, J=8 Hz, 1H), 8.13 (s, 1H), 8.07-8.05 (d, J=8 Hz, 1H), 7.48-7.47 (d, J=4 Hz, 1H), 7.34-7.32 (d, J=8 Hz, 1H), 7.07-7.05 (m, 2H), 4.77-4.71 (m, 1H), 4.15 (s, 3H), 1.32-1.31 (d, J=4 Hz, 6H); MS: MS m/z 328.20 (M++1).

Workup

  1. waitdegasified again for 5 min at room temperature
  2. customThe reaction vessel (Pressure tube) was sealed
  3. customThe reaction mass was evaporated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. customevaporated under reduced pressure
  8. customto get crude compound
  9. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-eef18e930f1b4636a5f09e74990a339d
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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