Sodium Carbonate → HCID 86673053, compound

HRID 1853285Notes

Reaction equation

HRID 1853285 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(O)C.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>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:14][CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 86673023HCID 86673023, compound

Product 1

HCID 86673053HCID 86673053, compoundYield 183.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube, a solution of 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (150 mg, 0.35 mmol) phenylboronic acid (60 mg, 0.49 mmol) a 2M aqueous solution of sodium carbonate (350 μl, 0.70 mmol) in toluene (2.4 ml) and ethanol (0.5 ml) was degassed with argon for 10 min and then tetrakis(triphenylphosphine)palladium (20 mg, 0.018 mmol) was added. The tube was sealed and the mixture was heated under argon at 120° C. for 4 hours. After cooling, the reaction mixture was poured onto a saturated solution of ammonium chloride and extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate and absorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-80%) to yield 2-Isoquinolin-3-yl-7-phenyl-chromen-4-one O-tert-butyl oxime (135 mg, 91%) as a yellow solid.

Workup

  1. customThe tube was sealed
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customabsorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-80%)

Sources & evidence

ORD record
ord-100c89f3b3144d97a479fd8f2aae14b6
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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