2,3-difluoro-N-phenylaniline

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

Procedure: 2,3-Difluoro-N-phenylaniline (100 mg, 0.487 mmol) and triphosgene (159 mg, 0.536 mmol) were dissolved in CH2Cl2 (1 mL). The solution was cooled in an ice bath, and pyridine (79 μL, 0.975 mmol) was added slowly. Upon complete addition, the reaction was warmed to room temperature and stirred for 1 h. Then, it was cooled in an ice bath and quenched by the slow addition of H2O (1 mL). The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL). The aqueous layer was extracted again with CH2Cl2 (5 mL). The organic layers were combined and washed once with H2O (10 mL), dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to yield the title compound as a light brown oil (114.7 mg). The solution was cooled in an ice bath Upon complete addition Then, it was cooled in an ice bath quenched by the slow addition of H2O (1 mL) The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL) The aqueous layer was extracted again with CH2Cl2 (5 mL) washed once with H2O (10 mL) dried over MgSO4 concentrated The residue was purified by silica gel column chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-bromo-2,3-difluorobenzene (0.232 mL, 2.073 mmol), aniline (0.208 mL, 2.280 mmol), Pd2(dba)3 (95 mg, 0.104 mmol), BINAP (194 mg, 0.311 mmol), sodium tert-butoxide (299 mg, 3.11 mmol), and toluene (3 mL) in a sealed vessel under argon was heated in an oil bath at 110° C. overnight. The reaction mixture was filtered through a plug of celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography to give the title compound as a light brown oil (411 mg). LCMS m/z=206.1 [M+H]+; 1H NMR (400 MHz, Methanol-d4) δ ppm 6.53-6.64 (m, 1H), 6.80-6.88 (m, 2H), 6.88-6.95 (m, 1H), 6.95-7.03 (m, 2H), 7.11-7.19 (m, 2H). The reaction mixture was filtered through a plug of celite The filtrate was concentrated the residue was purified by silica gel column chromatography

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

Procedure: 2,3-Difluoro-N-phenylaniline (100 mg, 0.487 mmol) and triphosgene (159 mg, 0.536 mmol) were dissolved in CH2Cl2 (1 mL). The solution was cooled in an ice bath, and pyridine (79 μL, 0.975 mmol) was added slowly. Upon complete addition, the reaction was warmed to room temperature and stirred for 1 h. Then, it was cooled in an ice bath and quenched by the slow addition of H2O (1 mL). The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL). The aqueous layer was extracted again with CH2Cl2 (5 mL). The organic layers were combined and washed once with H2O (10 mL), dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to yield the title compound as a light brown oil (114.7 mg). The solution was cooled in an ice bath Upon complete addition Then, it was cooled in an ice bath quenched by the slow addition of H2O (1 mL) The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL) The aqueous layer was extracted again with CH2Cl2 (5 mL) washed once with H2O (10 mL) dried over MgSO4 concentrated The residue was purified by silica gel column chromatography

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

Procedure: 2,3-Difluoro-N-phenylaniline (100 mg, 0.487 mmol) and triphosgene (159 mg, 0.536 mmol) were dissolved in CH2Cl2 (1 mL). The solution was cooled in an ice bath, and pyridine (79 μL, 0.975 mmol) was added slowly. Upon complete addition, the reaction was warmed to room temperature and stirred for 1 h. Then, it was cooled in an ice bath and quenched by the slow addition of H2O (1 mL). The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL). The aqueous layer was extracted again with CH2Cl2 (5 mL). The organic layers were combined and washed once with H2O (10 mL), dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to yield the title compound as a light brown oil (114.7 mg). The solution was cooled in an ice bath Upon complete addition Then, it was cooled in an ice bath quenched by the slow addition of H2O (1 mL) The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL) The aqueous layer was extracted again with CH2Cl2 (5 mL) washed once with H2O (10 mL) dried over MgSO4 concentrated The residue was purified by silica gel column chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-bromo-2,3-difluorobenzene (0.232 mL, 2.073 mmol), aniline (0.208 mL, 2.280 mmol), Pd2(dba)3 (95 mg, 0.104 mmol), BINAP (194 mg, 0.311 mmol), sodium tert-butoxide (299 mg, 3.11 mmol), and toluene (3 mL) in a sealed vessel under argon was heated in an oil bath at 110° C. overnight. The reaction mixture was filtered through a plug of celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography to give the title compound as a light brown oil (411 mg). LCMS m/z=206.1 [M+H]+; 1H NMR (400 MHz, Methanol-d4) δ ppm 6.53-6.64 (m, 1H), 6.80-6.88 (m, 2H), 6.88-6.95 (m, 1H), 6.95-7.03 (m, 2H), 7.11-7.19 (m, 2H). The reaction mixture was filtered through a plug of celite The filtrate was concentrated the residue was purified by silica gel column chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-bromo-2,3-difluorobenzene (0.232 mL, 2.073 mmol), aniline (0.208 mL, 2.280 mmol), Pd2(dba)3 (95 mg, 0.104 mmol), BINAP (194 mg, 0.311 mmol), sodium tert-butoxide (299 mg, 3.11 mmol), and toluene (3 mL) in a sealed vessel under argon was heated in an oil bath at 110° C. overnight. The reaction mixture was filtered through a plug of celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography to give the title compound as a light brown oil (411 mg). LCMS m/z=206.1 [M+H]+; 1H NMR (400 MHz, Methanol-d4) δ ppm 6.53-6.64 (m, 1H), 6.80-6.88 (m, 2H), 6.88-6.95 (m, 1H), 6.95-7.03 (m, 2H), 7.11-7.19 (m, 2H). The reaction mixture was filtered through a plug of celite The filtrate was concentrated the residue was purified by silica gel column chromatography

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

Procedure: 2,3-Difluoro-N-phenylaniline (100 mg, 0.487 mmol) and triphosgene (159 mg, 0.536 mmol) were dissolved in CH2Cl2 (1 mL). The solution was cooled in an ice bath, and pyridine (79 μL, 0.975 mmol) was added slowly. Upon complete addition, the reaction was warmed to room temperature and stirred for 1 h. Then, it was cooled in an ice bath and quenched by the slow addition of H2O (1 mL). The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL). The aqueous layer was extracted again with CH2Cl2 (5 mL). The organic layers were combined and washed once with H2O (10 mL), dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to yield the title compound as a light brown oil (114.7 mg). The solution was cooled in an ice bath Upon complete addition Then, it was cooled in an ice bath quenched by the slow addition of H2O (1 mL) The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL) The aqueous layer was extracted again with CH2Cl2 (5 mL) washed once with H2O (10 mL) dried over MgSO4 concentrated The residue was purified by silica gel column chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-bromo-2,3-difluorobenzene (0.232 mL, 2.073 mmol), aniline (0.208 mL, 2.280 mmol), Pd2(dba)3 (95 mg, 0.104 mmol), BINAP (194 mg, 0.311 mmol), sodium tert-butoxide (299 mg, 3.11 mmol), and toluene (3 mL) in a sealed vessel under argon was heated in an oil bath at 110° C. overnight. The reaction mixture was filtered through a plug of celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography to give the title compound as a light brown oil (411 mg). LCMS m/z=206.1 [M+H]+; 1H NMR (400 MHz, Methanol-d4) δ ppm 6.53-6.64 (m, 1H), 6.80-6.88 (m, 2H), 6.88-6.95 (m, 1H), 6.95-7.03 (m, 2H), 7.11-7.19 (m, 2H). The reaction mixture was filtered through a plug of celite The filtrate was concentrated the residue was purified by silica gel column chromatography