Methanol → Methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate

HRID 1986454Notes

Reaction equation

HRID 1986454 reaction equation
[CH2:1]([C:5]1[C:14]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:13]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:11]=2)[N:6]=1)[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.C[OH:47].[C]=O.[O:50]1[CH2:54]CC[CH2:51]1>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>[C:19]([O:18][C:17]([NH:16][CH2:15][C:14]1[C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])=[N:6][C:7]2[C:12]([C:13]=1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)=[CH:11][C:10]([C:51]([O:50][CH3:54])=[O:47])=[CH:9][CH:8]=2)=[O:23])([CH3:20])([CH3:22])[CH3:21]

Participants

9

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 510503433-{[(Tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl trifluoromethanesulfonateHCID 178418416HCID 178418416, compound

Product 1

HCID 68831784Methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylateYield 67%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of tert-butyl [2-isobutyl-4-(4-methylphenyl)-6-trifluoromethanesulfonyloxy-quinolin-3-yl]methylcarbamate (12.16 g, 22 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.61 g, 1.1 mmol), palladium acetate (0.25 g, 1.1 mmol), triethylamine (3.4 ml, 24.2 mmol), methanol (30 ml) and tetrahydrofuran (50 ml) was stirred in a sealed tube under a 0.5 MPa carbon monoxide atmosphere at 100° C. for 3 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate (6.84 g, yield 67%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-65928cea5b2e467587d4b209d0abd844
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

Loading…