Potassium Carbonate → tert-Butyl 1,2,3,4-tetrahydroquinolin-4-ylcarbamate

HRID 1880618Notes

Reaction equation

HRID 1880618 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4](N)[CH2:3]C1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[C:27]([O:31][C:32](=[O:44])[NH:33][CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[NH:37][CH2:36][CH2:35]1)([CH3:30])([CH3:29])[CH3:28].BrC1C=C2C(=CC=1)NC=C2.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[C:27]([O:31][C:32](=[O:44])[NH:33][CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[NH:37][CH2:36][CH2:35]1)([CH3:30])([CH3:28])[CH3:29].[C:27]([O:31][C:32](=[O:44])[NH:33][CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:37]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[NH:1][CH:3]=[CH:4]3)[CH2:36][CH2:35]1)([CH3:30])([CH3:28])[CH3:29]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 249055-BromoindoleHCID 90495Di-tert-butyl dicarbonateHCID 4078484tert-Butyl 1,2,3,4-tetrahydroquinolin-4-ylcarbamateHCID 183840651,2,3,4-Tetrahydroquinolin-4-amine

Product 2

HCID 4078484tert-Butyl 1,2,3,4-tetrahydroquinolin-4-ylcarbamateHCID 67215878HCID 67215878, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst

Conditions

Temperature
100 °C

Procedure

(1,2,3,4-Tetrahydro-quinolin-4-yl)-carbamic acid tert-butyl ester was prepared by treatment of commercially available 1,2,3,4-tetrahydro-quinolin-4-ylamine (JW Pharmaceutical #7578-79-2) with BOC anhydride. The (1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid tert-butyl ester (1.28 g, 5.15 mmol), together with 5-bromoindole (0.67 g, 3.44 mmol), Pd2dba3 (0.063 g, 0.069 mmol), XPHOS (0.082 g, 0.17 mmol), potassium carbonate (1.2 g, 8.6 mmol) and tert-butabol (10 mL) were combined in a 50 mL tube. The tube was sealed and heated to 100° C. with stirring for 18 hours. The tube was then cooled to room temperature and the contents were partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic phase was separated and concentrated under reduced pressure, and the residue was purified by flash chromatography (0% to 25% EtOac/hexanes) to give 1.3 g of [1-(1H-indol-5-yl)-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic acid tert-butyl ester.

Workup

  1. customThe tube was sealed
  2. temperatureThe tube was then cooled to room temperature
  3. customthe contents were partitioned between EtOAc and saturated aqueous sodium bicarbonate
  4. customThe organic phase was separated
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by flash chromatography (0% to 25% EtOac/hexanes)

Sources & evidence

ORD record
ord-641c012dab5e48bb89c4890fb30bbdc1
Source dataset
uspto-grants-2012_11
Patent number
US08318770B2

Reaction notes

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