Extracurricular laboratory: Synthetic route of 1337533-31-9

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1337533-31-9.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H15BrFNO2

1.1-dimethylethyl 4-fluoro-5-(4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-yl)-2.3-dihydro-1H-indole-1-carboxylateA mixture of 1 , 1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (1 g, 3.16 mmol), PdCI2(dppf)*CH2CI2 adduct (0.129 g, 0.158 mmol), potassium acetate (0.776 g, 7.91 mmol) and bis(pinacolato)diboron (0.803 g, 3.16 mmol) in 1 ,4-dioxane (20 ml_) was stirred at 100 C overnight on a stirrer hot-plate. LCMS indicated complete conversion to the desired product. The reaction mixture was poured into 1 : 1 saturated aqueous NaCI: H20 (100 ml_) and ethyl acetate (100 ml_), shaken, and filtered through celite. The resulting mixture was separated and the aqueous layer was extracted with two additional portions of ethyl acetate (2 x 50 ml_). The combined organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (0-25% EtOAc in hexanes, 40 g silica gel column) to afford 1 , 1- dimethylethyl 4-fluoro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H- indole- 1-carboxylate (660 mg, 57.4 % yield) as a pale yellow oil. LC-MS(ES) m/z = 308 [M+H-tBu]+. H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12 H), 1.51 (s, 9 H), 3.05 (t, J = 8.72 Hz, 2 H), 3.98 (t, J = 8.72 Hz, 2 H), 7.22 – 7.61 (m, 2 H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1337533-31-9.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; MEDINA, Jesus Raul; CHARNLEY, Adam Kenneth; ROMERIL, Stuart Paul; WO2015/56180; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem