| 72% |
|
To a mixture of <strong>[387-48-4]3-fluoro-2-iodobenzoic acid</strong> (1 .4 g, 5.26 mmol), 1 H-pyrazole (0.72 g, 10.5 mmol), trans-N, N'-dimethyl-cyclohexane-1 ,2-diamine (0.17 mL, 1 .05 mmol), Cul (50.1 mg, 0.26 mmol), dioxane (50 mL) and water (0.028 mL) was added CS2CO3 (3.43 g, 10.5 mmol). The reaction mixture was heated to 100 C for 1 h. The reaction mixture was cooled to ambient temperature then diluted with water. The aqueous layer was acidified to pH2 and extracted with EtOAc (30 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. Purification (FCC), (DCM to 10%MeOH/1 %HOAC/DCM) afforded the title compound as a colorless oil (790 mg, 72%). 1H NMR (400 MHz, CDCI3): 7.85 - 7.73 (m, 1 H), 7.54 - 7.44 (m, 1 H), 7.44 - 7.34 (m, 1 H), 6.55 (s, 1 H). |
| 72% |
With caesium carbonate;copper(l) iodide; N,N?-trans-dimethyl cyclohexane-1,2-diamine; In 1,4-dioxane; water; at 100℃; for 1h; |
Intermediate 19: 3-Fluoro-2-(1 H-pyrazol-1 -yl)benzoic acid.To a mixture of <strong>[387-48-4]3-fluoro-2-iodobenzoic acid</strong> (1 .4 g, 5.26 mmol), 1 H-pyrazole (0.72 g, 10.5 mmol), trans-N, N'-dimethyl-cyclohexane-1 ,2-diamine (0.17 ml_, 1 .05 mmol), Cul (50.1 mg, 0.26 mmol), dioxane (50 ml_) and water (0.028 ml_) was added CS2CO3 (3.43 g, 10.5 mmol). The reaction mixture was heated to 100 C for 1 h. The reaction mixture was cooled to ambient temperature then diluted with water. The aqueous layer was acidified to pH 2 and extracted with EtOAc (30 ml_) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (S1O2, gradient DCM to 10% MeOH/1 %HOAC/DCM) to the yield the title compound as a colorless oil (790 mg, 72%). 1H NMR (400 MHz, CDCI3): 7.85 - 7.73 (m, 1 H), 7.54 - 7.44 (m, 1 H), 7.44 - 7.34 (m, 1 H), 6.55 (s, 1 H). |
| 72% |
With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 1h; |
Intermediate 93: 3-Fluoro-2-(1 H-pyrazol-1 -yl)benzoic acid.3-Fluoro-2-(1 H-pyrazol-1 -yl)benzoic acid. To a mixture of 3-fluoro-2- iodobenzoic acid (1 .4 g, 5.26 mmol), 1 H-pyrazole (0.72 g, 10.5 mmol), trans- N,N'-dimethyl-cyclohexane-1 ,2-diamine (0.17 mL, 1 .05 mmol), Cul (50.1 mg, 0.26 mmol), dioxane (50 mL) and water (0.028 mL) was added Cs2C03 (3.43 g, 10.5 mmol). The reaction mixture was heated to 100 C for 1 h. The reaction mixture was cooled to ambient temperature then diluted with water. The aqueous layer was acidified to pH2 and extracted with EtOAc (30 mL) three times. The organic layers were combined, dried over Na2S04, filtered and concentrated. Purification (FCC), (DCM to 10% MeOH/1 %HOAC/DCM) afforded the title compound as a colorless oil (790 mg, 72%). 1H NMR (400 MHz, CDCIs): 7.85 - 7.73 (m, 1 H), 7.54 - 7.44 (m, 1 H), 7.44 - 7.34 (m, 1 H), 6.55 (s, 1 H). |
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