Potassium Carbonate → HCID 86669228, compound

HRID 2366828Notes

Reaction equation

HRID 2366828 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(=O)([O-])[O-].[K+].[K+].[CH:29]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)=[O:30]>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>[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]([C:34]3[CH:35]=[CH:36][C:31]([CH:29]=[O:30])=[CH:32][CH:33]=3)[CH:15]=2)[N:10]([C:18](=[O:20])[CH3:19])[C@@H:9]([CH3:21])[CH2:8]1)[CH3:3]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 86669228HCID 86669228, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1-methylethyl[(cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Example 61) (1.6 g, 4.33 mmol), potassium carbonate (1.198 g, 8.67 mmol), tetrakis(triphenylphosphine)palladium(0) (0.250 g, 0.217 mmol) and (4-formylphenyl)boronic acid (0.780 g, 5.20 mmol) were dissolved in Ethanol (10 mL) and Toluene (10 mL). The reaction mixture was degassed for 30 min then stirred and heated under nitrogen for 1 hr at 100° C. The reaction mixture was filtered and the solvent evaporated under vacuum. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was dried through a hydrophobic frit and concentrated in vacuo. The residue was dissolved with dichloromethane and purified by SP4 on a 40+M silica cartridge using a gradient 20-75% ethyl acetate in cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the required product (1.4 g) as a yellow solid. LCMS (Method B): Rt 0.99, MH+=395

Workup

  1. customThe reaction mixture was degassed for 30 min
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent evaporated under vacuum
  4. customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
  5. customThe organic layer was dried through a hydrophobic frit
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved with dichloromethane
  8. custompurified by SP4 on a 40+M silica cartridge
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-f06583523b134457adcf0ae9a008de53
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…