Potassium Carbonate → HCID 70976575, compound

HRID 882238Notes

Reaction equation

HRID 882238 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:6][C@@H:5]1[CH3:23])(=[O:3])[CH3:2].[CH3:24][O:25][C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)=[O:27].C(=O)([O-])[O-].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].COCCOC.O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:31]3[CH:32]=[CH:33][C:28]([C:26]([O:25][CH3:24])=[O:27])=[CH:29][CH:30]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[CH2:6][C@@H:5]1[CH3:23])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 52933642HCID 52933642, compound

Product 1

HCID 70976575HCID 70976575, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

To a flask charged with tert-butyl ((2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate (for a preparation see Intermediate 29)(5 g, 13.05 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (2.58 g, 14.35 mmol), tetrakis(triphenylphosphine)palladium (0) (1.507 g, 1.305 mmol) and potassium carbonate (5.41 g, 39.1 mmol) was added DME (50 mL) and water (10.0 mL) and the resulting mixture was stirred at 100° C. under nitrogen for 1 h. The reaction was cooled to room temperature and most of the DME was evaporated in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. the residue was purified by chromatography, eluting with an EtOAc/hexanes gradient; which gave methyl 4-((2S,4R)-1-acetyl-4-((tert-butoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (5.35 g, 12.20 mmol, 94% yield) as a white foam. LCMS (HpH, 2 min), Rt=1.18 min, MH+=439.

Workup

  1. customwas evaporated in vacuo
  2. customThe residue was partitioned between EtOAc and water
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by chromatography
  9. washeluting with an EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-b180624a9bd04620a69894a1e40b5fb5
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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