Toluene → HCID 10296696, compound

HRID 987573Notes

Reaction equation

HRID 987573 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:17][CH:16]2[N:18]([CH2:19][CH2:20][NH2:21])[CH:13]([CH2:14][CH2:15]2)[CH:12]=1.Br[C:23]1[CH:24]=[C:25]([O:33][CH3:34])[CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[CH:28]2.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:34][O:33][C:25]1[CH:26]=[C:27]2[C:32](=[C:23]([NH:21][CH2:20][CH2:19][N:18]3[CH:16]4[CH2:15][CH2:14][CH:13]3[CH:12]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=3)[CH2:17]4)[CH:24]=1)[N:31]=[CH:30][CH:29]=[CH:28]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 2795998-bromo-6-methoxyquinolineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 18009179HCID 18009179, compound

Product 1

HCID 10296696HCID 10296696, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 0.17 g, (0.61 mmol) 2-[3-(2-naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethylamine, 0.13 g (0.55 mmol) 8-bromo-6-methoxyquinoline, 30 mg (0.03 mmol) Pd2(dba)3, 20 mg (0.08 mmol) 2-(di-t-butylphosphino)biphenyl and 10 mL PhMe is stirred at 23° C. for 16 h. The reaction mixture is poured into 100 mL of H2O and extracted 3×50 mL EtOAc. The combined organics are washed with 1×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered, and the volatiles are evaporated. The crude product is subjected to flash chromatography on SiO2, eluting with EtOAc to EtOAc/2M NH3 in MeOH (40/1), to give the title compound as an off-white solid. This solid is dissolved in 4 mL of absolute EtOH and treated with 0.01 g (0.14 mmol) (CO2H)2 to give 0.07 g (0.13 mmol, a 23% yield) of the oxalate salt of the title compound as a dark green solid: mp: 179-182 C; MS (ES) m/z 436 (MH)+.

Workup

  1. extractionextracted 3×50 mL EtOAc
  2. washThe combined organics are washed with 1×100 mL H2O, 1×100 mL brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe volatiles are evaporated
  6. washeluting with EtOAc to EtOAc/2M NH3 in MeOH (40/1)

Sources & evidence

ORD record
ord-ffad94cbbf8b488aa1cb912fedb2a0c2
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

Loading…