Methanol → HCID 68829895, compound

HRID 1986421Notes

Reaction equation

HRID 1986421 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:5]2[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C.CO.[C]=O.[C:42]([O:45][CH2:46]C)(=[O:44])C>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].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCCC1>[C:20]([O:19][C:18]([NH:17][CH2:16][C:6]1[C:7]([CH2:12][CH:13]([CH3:14])[CH3:15])=[N:8][C:9]2[C:4]([C:5]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[CH:3][C:2]([C:42]([O:45][CH3:46])=[O:44])=[CH:11][CH:10]=2)=[O:24])([CH3:23])([CH3:22])[CH3:21]

Participants

10

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86605625HCID 86605625, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 68829895HCID 68829895, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl (6-bromo-2-isobutyl-4-phenylquinolin-3-yl)methylcarbamate (0.79 g, 1.7 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.047 g, 0.084 mmol), palladium acetate (0.019 g, 0.084 mmol), triethylamine (0.26 ml, 1.9 mmol), methanol (10 ml) and tetrahydrofuran (10 ml) was stirred in a sealed tube under a 0.5 MPa carbon monoxide atmosphere at 110° C. for 3 hrs. The reaction mixture was cooled and added to a mixture of ethyl acetate (50 ml) and water (50 ml), and insoluble materials were filtered off. The organic layer was separated, washed with saturated brine (20 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography and crystallized from diisopropyl ether-ethyl acetate to give methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-phenylquinoline-6-carboxylate (0.71 g, yield 95%) as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationwere filtered off
  3. customThe organic layer was separated
  4. washwashed with saturated brine (20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography
  8. customcrystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-4cc28c13b0fd43b49868c5af401e5c59
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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