Potassium Carbonate → HCID 52934566, compound

HRID 2366954Notes

Reaction equation

HRID 2366954 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:22])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[N:10]([C:18](=[O:20])[CH3:19])[C@@H:9]([CH3:21])[CH2:8]1)[CH3:3].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:22])[O:4][CH:2]([CH3:3])[CH3:1])[CH2:8][C@@H:9]1[CH3:21])(=[O:20])[CH3:19]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 52934566HCID 52934566, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see example 4) (78.6 mg, 0.213 mmol), phenyl boronic acid (31.1 mg, 0.255 mmol), potassium carbonate (73.5 mg, 0.532 mmol) and tetrakis(triphenylphosphine)palladium(0) (12.30 mg, 10.64 μmol) in ethanol (2.5 mL) and toluene (2.5 mL) was degassed under house vacuum and quenched several times with nitrogen, and then was heated at 100° C. for 30 min before being cooled to room temperature. The mixture was filtered through celite and the insoluble washed with EtOH. Most of the solvent was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 25 to 55% AcOEt in hexanes) gave 1-methylethyl [(2S,4R)-1-acetyl-2-methyl-6-phenyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (71.6 mg, 0.195 mmol, 92%) as a white solid.

Workup

  1. customwas degassed under house vacuum
  2. customquenched several times with nitrogen
  3. temperaturebefore being cooled to room temperature
  4. filtrationThe mixture was filtered through celite
  5. washthe insoluble washed with EtOH
  6. concentrationMost of the solvent was concentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (gradient: 25 to 55% AcOEt in hexanes)

Sources & evidence

ORD record
ord-931526a7759049e78b51304111f9bc7e
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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