Dichloromethane → 7-[(4'-Tert-butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester

HRID 51920

Reaction equation

HRID 51920 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([NH:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1Br)[CH:10]=2)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].ClCCl.[C:35]([C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1)([CH3:38])([CH3:37])[CH3:36]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([NH:16][C:17]([C:18]1[C:19]([C:42]3[CH:43]=[CH:44][C:39]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:40][CH:41]=3)=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:25])[CH:10]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 698911587-(2-Bromobenzoylamino)quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 698914667-[(4'-Tert-butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl esterYield 87.5%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To 5 ml dioxane was added in sequence, 7-(2-bromobenzoylamino)quinoline-3-carboxylic acid ethyl ester (100 mg, 0.25 mmol), potassium carbonate (0.25 ml of 2.0M aqueous solution, 0.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene (6.9 mg, 0.0125 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (10.2 mg, 0.0125 mmol) and 4-tert-butylbenzeneboronic acid (111.5 mg, 0.63 mmol). The resulting mixture was degassed and placed under a nitrogen atmosphere. The degassing procedure was repeated 5 times and the reaction mixture was heated under reflux under nitrogen overnight. The reaction mixture was then cooled to room temperature and poured into water. The aqueous mixture was extracted with ethyl acetate and the ethyl acetate solution was washed with brine, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was purified by preparative thick layer chromatography, eluting with 60:40 hexane/ethyl acetate to yield the title compound (99 mg, 87.3% yield).

Workup

  1. customThe resulting mixture was degassed
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux under nitrogen overnight
  4. additionpoured into water
  5. extractionThe aqueous mixture was extracted with ethyl acetate
  6. washthe ethyl acetate solution was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness in vacuo
  9. customThe residue was purified by preparative thick layer chromatography
  10. washeluting with 60:40 hexane/ethyl acetate

Sources & evidence

ORD record
ord-eb795fd21c0d4831bfb772b80a48ee85
Source dataset
uspto-grants-2004_03
Patent number
US06713489B2

Linked notes

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