Dimethylformamide → HCID 50939865, compound

HRID 1618647Notes

Reaction equation

HRID 1618647 reaction equation
[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[NH:4][CH2:3]1.CN(C=O)C.[H-].[Na+].Cl[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[C:28]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:27]=1[CH3:42].N1C2C(=CC=CC=2)C=CC=1>CCOC(C)=O.C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[N:4]([C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]=[C:28]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:27]=2[CH3:42])[CH2:3]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 7047QuinolineHCID 24758Sodium hydrideHCID 12378945HCID 12378945, compoundHCID 672848583,3-Dimethyl-6-morpholinoindoline

Product 1

HCID 50939865HCID 50939865, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Under a N2 atmosphere, 3,3-dimethyl-6-morpholinoindoline (0.100 g, 0.430 mmol) was dissolved in DMF (2.00 mL, 26.0 mmol). Sodium hydride (0.0227 g, 0.947 mmol) was added and the reaction was stirred at rt for 12 minutes. The reaction was treated with 4-chloro-3-methyl-2-phenylquinoline (0.218 g, 0.861 mmol) and placed in a preheated oil bath at 140° C. for 2 h. LCMS showed no starting quinoline remained. The reaction was diluted with EtOAc and 2% sodium bicarbonate. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography eluting with 20% to 50% EtOAc in hexane, and then purified again by preparative reverse phase chromatography to give 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-3-methyl-2-phenylquinoline. Mass Spectrum (ESI) m/e=450.2 (M+1)

Workup

  1. waitplaced in a preheated oil bath at 140° C. for 2 h
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography
  6. washeluting with 20% to 50% EtOAc in hexane
  7. custompurified again by preparative reverse phase chromatography

Sources & evidence

ORD record
ord-465b37ba5163458497aac50495c2e078
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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