Extended knowledge of 1337533-31-9

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate, A new synthetic method of this compound is introduced below., name: tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate, A new synthetic method of this compound is introduced below., name: tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate

1.1 -dimethylethyl 4-fluoro-5-(4.4.5.5-tetrameth yl-1.3.2-dioxaborolan-2-yl)-2.3-dih vdro-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 NaCI(aq. sat.): 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]+. 1H 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).

The synthetic route of 1337533-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem