1-(TRIISOPROPYLSILYL)PYRROLE

n-BuLi (1.57 M in n- hexane, 17.3 mL, 27.1 mmol) was added dropwise to the solution of pyrrole (19, 1.52 g, 22.6 mmol) in THF (36 mL) at -78 °C, and the whole mixture was stirred for 30 min at -78 °C. TIPSCl (5.3 mL, 24.9 mmol) was added to the mixture, and the whole mixture was stirred for 5 hr at -78 °C. Sat. NH4Cl aq. was added to the mixture at 0 °C, and the whole mixture was extracted with AcOEt. Removal of the solvent from the AcOEt extract under reduced pressure gave a crude product, which was purified by SiO2 column (n-hexane/AcOEt = 10:1) to give 1-triisopropylsilanyl-1H-pyrrole (4.94 g, 98percent) as a colorless oil.To a stirred suspension of Sodium Hydride (2.68 g, 60percent in oil, 0.11 17 mol) in dry THF (50 mL) was added dropwise pyrrole (5.0 g) at 0 °C. Reaction mixture was stirred at same temperature for 1.0 h. Then triisopropyl silyl chloride (18.67 g, 0.09688 mol) was added dropwise at 0 °C. Resulting reaction mixture was then stirred at below 10 °C for 2 h. After completion of reaction, ice water was added (75 mL) and mixture was then extracted with diethyl ether (2 x 75 mL). Combined organic layer was then washed with water (100 mL). Organic layer was dried over sodium sulphate and evaporated under vacuum afforded red oily crude compound (15.5 g, 93.09percent yield). This crude was forwarded as it is in next step.n-Butyllithium in hexane (2.2 mL of a 2.5 M solution, 5.5 mmol) was added dropwise to argon-dried pyrrole (compound 2) (335 mg, 5.0 mmol) in 10 mL of anhydrous THF at -78 °C. Triisopropylsilyl chloride (965 mg, 5.0 mmol) was added after 10 min and the reaction warmed to room temperature. To a stirred solution of IH-pyrrole (V) (3.0 g, 44.7 mmol) in THF (100 mL) was added w-BuLi (30.7 mL, 49.1 mmol; 1.6 solution in hexane) at -78 °C and maintained for 30 min at the same temperature under argon atmosphere. To the reaction mixture was added triisopropylsilyl chloride (9.56 mL, 44.7 mmol) at -78 °C and the resulting reaction mixture was allowed to warm to RT and then stirred for additional 30 min. After complete consumption of the starting material (monitored by TLC), the reaction mixture was quenched with saturated aq. NH0237] 1-triisopropylsiIanyl-lH-pyrrole (20):; To a solution of lH-pyrrole (18) (5 g, 74.Step 92a: 3-Bromo-1-(triisopropylsilyl)-1H-pyrrole (Compound 0601-197)[0606]A solution n-BuLi in THF (2.5 M, 19.6 mL, 49 mmol) was added to a stirred solution of pyrrole (3 g, 44.7 mmol) in anhydrous THF (20 mL) at −78° C. in an N

Molecular Weight:223.43
Rotatable Bond Count:4
Exact Mass:223.175626336
Monoisotopic Mass:223.175626336
Topological Polar Surface Area:4.9
Heavy Atom Count:15
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes