Potassium Carbonate → HCID 52935453, compound

HRID 2366935Notes

Reaction equation

HRID 2366935 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].CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)O1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[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:31]3[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=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 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 52935453HCID 52935453, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A flask was charged with 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see example 4) (739 mg, 2 mmol), [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (570 mg, 2.60 mmol), potassium carbonate (691 mg, 5.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (146 mg, 0.200 mmol) then filled with 1,4-dioxane (9 mL) and water (3 mL) and purged with nitrogen. The mixture was stirred under microwave irradiation for 30 min at 120° C. then cooled to room temperature. Most of the 1,4-dioxane was removed in vacuo and the residue was partitioned between water and AcOEt. The layers were separated and the aqueous phase extracted twice with AcOEt. The combined organic phases were washed twice with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 25 G silica cartridge (gradient: 13 to 63% AcOEt in Hexanes) gave 1-methylethyl[(2S,4R)-1-acetyl-6-(4-aminophenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (660 mg, 1.730 mmol, 87% yield) as a pale yellow foam.

Workup

  1. customfor a preparation
  2. custompurged with nitrogen
  3. temperaturethen cooled to room temperature
  4. customMost of the 1,4-dioxane was removed in vacuo
  5. customthe residue was partitioned between water and AcOEt
  6. customThe layers were separated
  7. extractionthe aqueous phase extracted twice with AcOEt
  8. washThe combined organic phases were washed twice with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by SP4

Sources & evidence

ORD record
ord-6757ada07f5349b1964544e8af4daba0
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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