Dichloromethane → HCID 58388083, compound

HRID 2080236Notes

Reaction equation

HRID 2080236 reaction equation
[OH:1][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].ClCCl.C(N(CC)CC)C.[N+:32]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)([O-:34])=[O:33]>C(#N)C.O.FC(F)(F)C(O)=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N+:32]([C:35]1[CH:40]=[CH:39][C:38]([O:1][C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=2)[CH2:5][NH:6][C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)=[O:8])=[CH:37][CH:36]=1)([O-:34])=[O:33]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27735524-Nitrophenylboronic acidHCID 58875319HCID 58875319, compound

Product 1

HCID 58388083HCID 58388083, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6422Trifluoroacetic acidSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a mixture solution of quinoline-6-carboxylic acid 3-hydroxybenzylamide described in Preparation Example E+-4 (3.0 mg, 0.011 mmol), copper(II) acetate (2.9 mg, 0.016 mmol), molecular sieves 4A (50 mg) and dichloromethane (2 mL) were added triethylamine (0.0077 mL, 0.055 mmol) and 4-nitrophenylboronic acid (1.8 mg, 0.011 mmol), and the solution was stirred in the presence of air at room temperature for 10 days. The reaction solution was filtered, then, water, ethyl acetate and an aqueous solution of 29% ammonia 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 (1.14 mg, 0.0022 mmol, 20%) was obtained.

Workup

  1. filtrationThe reaction solution was filtered
  2. additionwater, ethyl acetate and an aqueous solution of 29% ammonia were added for extraction
  3. washthe solution was washed with brine
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ba270864091a49f49744e53fbd5060bf
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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