HCID 86668194, compound → HCID 68109185, compound

HRID 2174635Notes

Reaction equation

HRID 2174635 reaction equation
[CH3:1][C:2]1([CH3:31])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](OS(C(F)(F)F)(=O)=O)([C:13]2[CH:14]=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:5][CH2:4][CH2:3]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:31])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:14]=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:5][CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 86668194HCID 86668194, compound

Product 1

HCID 68109185HCID 68109185, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Quinoline boronic acid triol salt (compound no. C2-12) (0.46 g, 1.56 mmol) synthesized by the method of Example 9, trifluoromethanesulfonic acid 5,5-dimethyl-1-(3-quinolinyl)-4,5-dihydro-3H-2-benzazepin-1-yl ester (0.5 g, 1.56 mmol) and tetrakistriphenyl phosphine palladium (0.86 g, 0.31 mmol) were added to 5 mL of toluene. After sparging with nitrogen gas, the resulting reaction solution was heated to reflux, and maintained for 14 hours. Then the reaction solution was cooled to room temperature and poured into ice water, followed by extracting with ethyl acetate. The organic layer was washed with brine, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=3:1) to obtain the target compound (0.06 g, yield: 13%).

Workup

  1. customAfter sparging with nitrogen gas
  2. customthe resulting reaction solution
  3. temperaturewas heated
  4. temperatureto reflux
  5. temperaturemaintained for 14 hours
  6. extractionby extracting with ethyl acetate
  7. washThe organic layer was washed with brine
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-555d0f782a4849d79cc4e388349ef195
Source dataset
uspto-grants-2015_06
Patent number
US09062024B2

Reaction notes

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