2,4,6-trifluoroaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2,4,6-trifluoroaniline (127 mg, 1 mmol) was added 1N NaHMDS in THF (0.9 mL, 0.9 mmol). The mixture stirred for 15 min at rt. Methyl 3-{3-[2-({5-fluoro-2-(methyloxy)-4-[2-(1-piperidinyl)ethyl]phenyl}amino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl}benzoate (Example 128, step A) (100 mg, 0.172 mmol) in 3 mL of dry THF was added. The mixture stirred at rt for 30 minutes. 1 mL of MeOH was added followed by 1 g of silica gel. The solvent was rotovaped down and the pre-adsorbed solids were purified by flash chromatography to give the title compound (74 mg, 0.11 mmol, 62%). 1H NMR (400 MHz, CDCl3) δ ppm 9.44 (d, J=6.96 Hz, 1H), 8.20-8.26 (m, 4H), 7.99 (dt, J=7.83, 1.40 Hz, 1H), 7.74-7.78 (m, 2H), 7.62 (d, J=8.97 Hz, 1H), 7.48 (t, J=7.78 Hz, 1H), 7.31-7.36 (m, 1H), 6.91 (td, J=6.87, 1.28 Hz, 1H), 6.72-6.78 (m, 3H), 6.60 (d, J=5.13 Hz, 1H), 3.90 (s, 3H), 2.78-2.84 (m, 2H), 2.53-2.58 (m, 2H), 2.44-2.53 (m, 4H), 1.58-1.65 (m, J=5.59, 5.59, 5.59, 5.59 Hz, 4H), 1.46 (d, J=5.13 Hz, 2H). MS (ESI): 696 [M+H]+. The mixture stirred at rt for 30 minutes the pre-adsorbed solids were purified by flash chromatography