Nitrogen → (1-Benzyl-6-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester

HRID 1363092Notes

Reaction equation

HRID 1363092 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+].N#N>CCO.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:15]=2)[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59297053(1-Benzyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 59778198(1-Benzyl-6-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl esterYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Compound 89A (150 mg, 0.36 mmol), phenylboronic acid (57 mg, 0.47 mmol) and 2N aqueous Na2CO3 (1.25 mL, 2.5 mmol) in a mixed solvent of toluene (1.5 mL) and EtOH((0.5 mL) were stirred at RT for 30 min while N2 was allowed to bubble through the mixture, and then tetrakis(triphenylphosphine)-palladium (0) (30 mg) was added. The mixture was stirred at 90° C. under N2 for 1 h. After cooling to RT, the mixture was extracted with EtOAc (15 mL×3), and organic extracts were washed with brine, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc (10-50%) in hexane to give the title compound (80 mg, 67%) as a white foam.

Workup

  1. customto bubble through the mixture
  2. additiontetrakis(triphenylphosphine)-palladium (0) (30 mg) was added
  3. temperatureAfter cooling to RT
  4. extractionthe mixture was extracted with EtOAc (15 mL×3), and organic extracts
  5. washwere washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe resulting residue was chromatographed (silica gel)
  9. washeluting with EtOAc (10-50%) in hexane

Sources & evidence

ORD record
ord-e2f796908b5a47339594657420fb1606
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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