Dimethylamine → N-[6-Dimethylamino-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide

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Reaction Steps

In a sealed tube, heat N-[6-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 35) (200 mg, 0.45 mmol), dimethyl amine (2.0 M in tetrahydrofuran, 0.45 mL, 0.90 mmol), palladium acetate (5 mg, 0.002 mmol), sodium tert-butoxide (133 mg, 1.38 mmol), and 1,2,3,4,5-pentaphenyl-1′-(di-t-butylphosphino)ferrocene ligand (60 mg, 0.008 mmol) in toluene (5 mL) at 70° C. overnight. Cool to room temperature, dilute with ethyl acetate/10% potassium carbonate, and filter off the red suspension. Wash the organic portion with 10% aqueous potassium carbonate (2×), dry over anhydrous sodium sulfate, filter, and concentrate. Purify the residue by silica gel column chromatography eluting with 40 to 100% ethyl acetate/hexanes to obtain the title compound (135 mg, 74%). MS (ES): m/z 408 (M+1); 1H NMR (CD3OD): δ 7.25 (m, 1H), 7.18 (d, 1H), 7.01 (s, 1H), 6.96 (t, 1H), 6.89 (d, 1H), 6.81 (d, 1H), 6.65 (d, 1H), 5.30 (s, 2H), 4.19 (m, 1H), 3.08 (dd, 1H), 2.88 (s, 6H), 2.77 (m, 2H), 2.63 (m, 1H), 2.50 (m, 1H), 2.12 (m, 1H), 1.97 (m, 1H), 1.18 (m, 6H).

Provenance & Evidence