4522-35-4, The chemical industry reduces the impact on the environment during synthesis 4522-35-4, name is 3-Iodo-1H-pyrazole, I believe this compound will play a more active role in future production and life.
NaH (60% dispersion in mineral oil, 143 mg, 3.57 mmol) was added to a stirred solution of 3-iodo-lH-pyrazole [4522-35-4] (659 mg, 4.00 mmol) in DMF (20 mL) at 0 C under N2 atmosphere. The mixture was stirred at room temperature for 30 min. 2- (Trimethylsilyl)ethoxymethyl chloride [76513-69-4] (0.66 mL, 3.74 mmol) was added at 0 C and the reaction mixture was stirred at room temperature for 16 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane, gradient from 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to afford a mixture of 1-188 and 1-189 (965 mg, 86%).; Cul (28.3 mg, 0.15 mmol), N,N?-dimethylcyclo hexane- 1, 2-diamine (46.9 uL, 0.30 mmol) and K2C03 (411 mg, 2.98 mmol) were added to a solution of 1-188 and 1-189 (965 mg, 2.98 mmol) in l,4-dioxane (10 mL) in a sealed tube while nitrogen was bubbling. After 10 min, 4-chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (227 mg, 1.49 mmol) was added. The reaction mixture was stirred at room temperature for 10 min, and at 100 C for 20 h. The mixture was diluted with water and extracted with EtOAc. The combined organic extarcts were dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane, gradient from 0/100 to 15/85). The desired fractions were collected and concentrated in vacuo to afford a mixture of 1-190 and I- 191 (270 mg, 51%).; Pd2dba3 (39.1 mg, 42.6 pmol), XantPhos (61.7 mg, 0.11 mmol) and CS2CO3 (521 mg, 1.60 mmol) were added to a solution of 1-190 and 1-191 (372 mg mg, 1.07 mmol) in anhydrous DMF (12 mL) in a sealed tube while nitrogen was bubbling. After 10 min, 2,6-dichloro-4-fluoroaniline [344-19-4] (249 mg, 1.39 mmol) was added. The reaction mixture was stirred at room temperature for 10 min, and at 100 C for 20 h. The mixture was filtered over a pad of Celite and the filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane, gradient from 0/100 to 100/0).). The desired fractions were collected and concentrated in vacuo to afford a mixture of I- 192 and 1-193 (376 mg, 71 %).
The chemical industry reduces the impact on the environment during synthesis 3-Iodo-1H-pyrazole. I believe this compound will play a more active role in future production and life.