Uses
Reactant for preparation of:• ;Indoleacetic acid analogs as differentiation-inducing and antiproliferative agents for human myeloblastoma cells1• ;Indole-carboxamide derivatives as inhibitors of lipid peroxidation and superoxide anion formation2• ;Indole carboxamides as hyaluronidase inhibitors3• ;Fuconojirimycin derivatives as inhibitors of α-fucosidases4• ;Indole-2 and 3-carboxamides as selective cyclooxygenase-2 inhibitors5• ;Indole amides as antihistaminic agents6
Synthesis
1. 0.50 g (3.10 mmol) 1H-indole-3-carboxylic acid was dissolved in 5 mL of anhydrous DMF under dry conditions and stirred until completely dissolved.
2. 0.27 g (6.75 mmol) of 60% NaH (dispersed in mineral oil) was added slowly and the reaction was stirred at room temperature for 30 minutes.
3. Add 0.39 mL (3.28 mmol) of benzyl bromide dropwise and continue stirring at room temperature for 1 hour.
4. The reaction mixture was slowly poured into ice water and extracted with ethyl acetate (3 × 10 mL).
5. The organic phases were combined, dried over anhydrous NaSO, filtered and concentrated under reduced pressure.
6. The residue was recrystallized from ether to give 0.61 g (78% yield) of white crystals of 1-benzyl-1H-indole-3-carboxylic acid. 7. The product was subjected to electrospray ionization mass spectrometry (ESI).
7. The product was characterized by electrospray ionization mass spectrometry (ES-MS): m/z 250 [M-H]
References
[1] Patent: US2007/27173, 2007, A1. Location in patent: Page/Page column 35
[2] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7114 - 7117
[3] Tetrahedron, 2016, vol. 72, # 5, p. 734 - 745
