Water → HCID 58387934, compound

HRID 2080238Notes

Reaction equation

HRID 2080238 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].O1CCCC1.[CH2:27]([Mg]Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C(#N)C.O.FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH2:27]([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])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 58875334HCID 58875334, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 58387934HCID 58387934, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolvent2×HCID 8857Ethyl AcetateSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a mixture of quinoline-6-carboxylic acid 3-bromobenzylamide described in Preparation Example E+-8 (8.0 mg, 0.023 mmol), dichloro(1,1′-bis(diphenylphosphino)ferrocene)nickel(II) (3.2 mg, 0.0047 mmol) and tetrahydrofuran (1 mL) was added benzylmagnesium chloride (1.1M tetrahydrofuran solution, 0.088 mL, 0.094 mmol) at room temperature, and the solution was stirred for 30 minutes at 50° C. After cooling, water and ethyl acetate were added for extraction, the solution was washed with brine, the solvent was then 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 (2.1 mg, 0.0045 mmol, 19%) was obtained.

Workup

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

Sources & evidence

ORD record
ord-4fd71c99aea54d3caf6267e27c17255b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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