Toluene → HCID 58387947, compound

HRID 2080237Notes

Reaction equation

HRID 2080237 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2)=[O:8].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[F:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1>C(#N)C.O.FC(F)(F)C(O)=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.C(O)(=O)C.C(OCC)(=O)C.O.CO>[F:35][C:36]1[CH:41]=[C:40]([C:2]2[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][NH:6][C:7]([C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[N:15]=[CH:14][CH:13]=[CH:12]4)=[O:8])[CH:3]=2)[CH:39]=[CH:38][CH:37]=1

Participants

12

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 58875334HCID 58875334, compound

Product 1

HCID 58387947HCID 58387947, compoundYield 8.3%

Reagents, catalysts & solvents 7

HCID 178418397HCID 178418397, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent2×HCID 8857Ethyl AcetateSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

To a mixture of quinoline-6-carboxylic acid 3-bromobenzylamide described in Preparation Example E+-8 (4.0 mg, 0.012 mmol), toluene (1 mL) and methanol (0.25 mL) were added an aqueous solution of 2M sodium carbonate (0.5 mL), tetrakis(triphenylphosphine)palladium(0) (1.4 mg, 0.0012 mmol) and 3-fluorophenylboronic acid (1.7 mg, 0.012 mmol), and the solution was stirred at 70° C. for 4 hours. After cooling, water, ethyl acetate and acetic acid were added for extraction, the solution was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound (0.47 mg, 0.0010 mmol, 8.3%) was obtained.

Workup

  1. temperatureAfter cooling
  2. washthe solution was washed with brine
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b8c2f5e6a1834735b3392ec04acec93c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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