C1COCCN1.Cc1cccc(C)c1C(=O)NC(c1cccc(Br)c1)C12CCC(CC1)N2C>CC(=O)O.CC(=O)O.CC(C)(C)[O-].Cc1ccccc1.[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>Cc1cccc(C)c1C(=O)NC(c1cccc(N2CCOCC2)c1)C12CCC(CC1)N2CTo a suspension of N-((3-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (0.040 g, 0.09 mmol), MORPHOLINE (8.97 µL, 0.10 mmol), BINAP (5.83 mg, 9.36 µmol), and sodium tert-butoxide (0.013 g, 0.14 mmol) in toluene (2 mL) was added palladium(II) acetate (1.051 mg, 4.68 µmol). Nitrogen was passed through the solution for 15 min prior to being heated at 80 °C overnight. Crude LC shows starting material still present. Heated to 110oC for 2 days. Reaqction no longer progressing. Reaction mixture was concentrated in vacuo. Material was diluted with ethyl acetate, filtered thru celite and concentrated in vacuo. Submitted to purification group (52 mg in 1.6 mL DMSO). Received back dried- down fractions. Diluted with DCM, combined and concentrated to afford 2,6-dimethyl-N-((7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)(3-morpholinophenyl)methyl)benzamide (7.30 mg, 17.99 %) Submitted 4.5 mg Vial # 26243972 (TWOC): 7.0545 g
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