N-(2,2,2-trifluoroethyl)aniline

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

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

Procedure: To a solution of 2,2,2-trifluoro-N-phenylacetamide (5.0 g, 26 mmol) in THF (10 mL) was added BH3 in THF (130 mL, 130 mmol, 1.0 M). The resulting mixture was refluxed overnight. The mixture was quenched with water and methanol, concentrated to remove most of THF, and extracted with EtOAc. Organics were washed with brine, dried (Na2SO4), and concentrated to give 4.17 g (92%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71-3.75 (2H, m), 6.66 (2H, d, J=8.0 Hz), 6.79 (1H, t, J=7.2 Hz), 7.20 (2H, t, J=8.0 Hz). The resulting mixture was refluxed overnight The mixture was quenched with water and methanol concentrated to remove most of THF extracted with EtOAc Organics were washed with brine dried (Na2SO4) concentrated

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

Procedure: To a solution of 2,2,2-trifluoro-N-phenylacetamide (5.0 g, 26 mmol) in THF (10 mL) was added BH3 in THF (130 mL, 130 mmol, 1.0 M). The resulting mixture was refluxed overnight. The mixture was quenched with water and methanol, concentrated to remove most of THF, and extracted with EtOAc. Organics were washed with brine, dried (Na2SO4), and concentrated to give 4.17 g (92%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71-3.75 (2H, m), 6.66 (2H, d, J=8.0 Hz), 6.79 (1H, t, J=7.2 Hz), 7.20 (2H, t, J=8.0 Hz). The resulting mixture was refluxed overnight The mixture was quenched with water and methanol concentrated to remove most of THF extracted with EtOAc Organics were washed with brine dried (Na2SO4) concentrated

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

Procedure: To a solution of 2,2,2-trifluoro-N-phenylacetamide (5.0 g, 26 mmol) in THF (10 mL) was added BH3 in THF (130 mL, 130 mmol, 1.0 M). The resulting mixture was refluxed overnight. The mixture was quenched with water and methanol, concentrated to remove most of THF, and extracted with EtOAc. Organics were washed with brine, dried (Na2SO4), and concentrated to give 4.17 g (92%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71-3.75 (2H, m), 6.66 (2H, d, J=8.0 Hz), 6.79 (1H, t, J=7.2 Hz), 7.20 (2H, t, J=8.0 Hz). The resulting mixture was refluxed overnight The mixture was quenched with water and methanol concentrated to remove most of THF extracted with EtOAc Organics were washed with brine dried (Na2SO4) concentrated

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

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

Procedure: To a solution of 2,2,2-trifluoro-N-phenylacetamide (5.0 g, 26 mmol) in THF (10 mL) was added BH3 in THF (130 mL, 130 mmol, 1.0 M). The resulting mixture was refluxed overnight. The mixture was quenched with water and methanol, concentrated to remove most of THF, and extracted with EtOAc. Organics were washed with brine, dried (Na2SO4), and concentrated to give 4.17 g (92%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71-3.75 (2H, m), 6.66 (2H, d, J=8.0 Hz), 6.79 (1H, t, J=7.2 Hz), 7.20 (2H, t, J=8.0 Hz). The resulting mixture was refluxed overnight The mixture was quenched with water and methanol concentrated to remove most of THF extracted with EtOAc Organics were washed with brine dried (Na2SO4) concentrated

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

Procedure: 250 mg (0.573 mmol) of (2,2,2-trifluoroethyl)phenyliodonium trifluoromethanesulfonate, 107 mg (1.15 mmol) of aniline and 5 ml of methylene chloride were reacted and worked up in the same manner as described in Reference Example 4 to obtain 91.1 mg of N-(2,2,2-trifluoroethyl)aniline as an oily substance. Yield, 92%.

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

Procedure: 200 mg (1.14 mmol) N-(2,2,2-trifluoroethyl)aniline and 1.14 mL (1.14 mmol) of a 1M sodium hydroxide solution were added dropwise to 212 mg (1.2 mmol) 6-chloropyrimidine-4-carboxylic acid chloride in 20 mL dichloromethane while cooling with a bath of ice and ethanol. The mixture was first stirred for 2 h with cooling and then stirred for 1 h at RT. 50 mL of a saturated sodium hydrogen carbonate solution were added and the mixture was stirred for 10 min. The organic phase was separated off, washed with water and 1M hydrochloric acid, dried on sodium sulphate, filtered and concentrated by rotary evaporation i.vac. with cooling stirred for 1 h at RT the mixture was stirred for 10 min The organic phase was separated off washed with water and 1M hydrochloric acid dried on sodium sulphate filtered concentrated by rotary evaporation i.vac

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

Procedure: 2.5 g (10.7 mmol) 2,2,2-trifluoroethyl trifluoromethanesulphonate were added to 2.0 g (21.5 mmol) aniline in 50 mL xylene and the mixture was refluxed for 2 days. After cooling, the mixture was filtered, washed with DIPE and the filtrate was evaporated down i.vac. The residue was purified by flash chromatography. The product fractions were combined and evaporated down i.vac. the mixture was refluxed for 2 days After cooling the mixture was filtered washed with DIPE the filtrate was evaporated down i.vac The residue was purified by flash chromatography evaporated down i.vac

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

Procedure: To a solution of 2,2,2-trifluoro-N-phenylacetamide (5.0 g, 26 mmol) in THF (10 mL) was added BH3 in THF (130 mL, 130 mmol, 1.0 M). The resulting mixture was refluxed overnight. The mixture was quenched with water and methanol, concentrated to remove most of THF, and extracted with EtOAc. Organics were washed with brine, dried (Na2SO4), and concentrated to give 4.17 g (92%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71-3.75 (2H, m), 6.66 (2H, d, J=8.0 Hz), 6.79 (1H, t, J=7.2 Hz), 7.20 (2H, t, J=8.0 Hz). The resulting mixture was refluxed overnight The mixture was quenched with water and methanol concentrated to remove most of THF extracted with EtOAc Organics were washed with brine dried (Na2SO4) concentrated

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

Procedure: To a solution of 2,2,2-trifluoro-N-phenylacetamide (5.0 g, 26 mmol) in THF (10 mL) was added BH3 in THF (130 mL, 130 mmol, 1.0 M). The resulting mixture was refluxed overnight. The mixture was quenched with water and methanol, concentrated to remove most of THF, and extracted with EtOAc. Organics were washed with brine, dried (Na2SO4), and concentrated to give 4.17 g (92%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71-3.75 (2H, m), 6.66 (2H, d, J=8.0 Hz), 6.79 (1H, t, J=7.2 Hz), 7.20 (2H, t, J=8.0 Hz). The resulting mixture was refluxed overnight The mixture was quenched with water and methanol concentrated to remove most of THF extracted with EtOAc Organics were washed with brine dried (Na2SO4) concentrated