Potassium Carbonate → HCID 52934330, compound

HRID 2366944Notes

Reaction equation

HRID 2366944 reaction equation
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH3:43][C:44]1[N:45]=[CH:46][NH:47][CH:48]=1.[CH3:49][CH:50]([O:52][C:53](=[O:70])[NH:54][C@H:55]1[C:64]2[C:59](=[CH:60][CH:61]=[C:62](Br)[CH:63]=2)[N:58]([C:66](=[O:68])[CH3:67])[C@@H:57]([CH3:69])[CH2:56]1)[CH3:51].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:51][CH:50]([O:52][C:53](=[O:70])[NH:54][C@H:55]1[C:64]2[C:59](=[CH:60][CH:61]=[C:62]([N:47]3[CH:48]=[C:44]([CH3:43])[N:45]=[CH:46]3)[CH:63]=2)[N:58]([C:66](=[O:68])[CH3:67])[C@@H:57]([CH3:69])[CH2:56]1)[CH3:49]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamateHCID 178418800HCID 178418800, compound

Product 1

HCID 52934330HCID 52934330, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of palladium(II) acetate (60 mg, 0.267 mmol) and Xantphos (380 mg, 0.797 mmol) in t-butanol (50 mL) and water (100 μL) was heated at 90° C. for 5 min. The hot solution was then added to a mixture of 4-methylimidazole (530 mg, 6.46 mmol), 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Example 4) (2.0 g, 5.4 mmol) and potassium carbonate (1.12 g, 8.1 mmol). The resulting mixture was refluxed for 24 h then cooled to room temperature and the insoluble were filtered off. Most of the solvents were removed in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 6% MeOH in DCM) gave 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (189 mg, 0.51 mmol, 9%)

Workup

  1. customfor a preparation
  2. temperatureThe resulting mixture was refluxed for 24 h
  3. temperaturethen cooled to room temperature
  4. filtrationthe insoluble were filtered off
  5. customMost of the solvents were removed in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (gradient: 0 to 6% MeOH in DCM)

Sources & evidence

ORD record
ord-38f6434e398e48ab8f06aa000524dc79
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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