5-Methoxy-1H-indole-2-carboxylic acid

LIGHT YELLOW TO BROWNISH POWDER

5-methoxyindole-2-carboxylic acid is an indolecarboxylic acid that is indole-2-carboxylic acid carrying an additional methoxy substituent at position 5. It has a role as a plant metabolite, a hypoglycemic agent and an EC 1.8.1.4 (dihydrolipoyl dehydrogenase) inhibitor. It is an indolecarboxylic acid and an aromatic ether.

To a solution of 2-Bromo-5-methoxy-1H-indole (1.0 g, 4.4 mmol, 1.0 equiv.) in dry THF (20 mL) at 0 C was added a 2 M solution of i-PrMgCl in THF(2.2 mL, 4.4 mmol, 1.0 equiv.) during 5 min. The clear solution was stirred at that temperature for anadditional 5 min, and a 2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) was addeddropwise during 5 min, while maintaining the temperature below 20 C. The resulting mixture wasstirred at that temperature for 0.5 h, dry CO2 (0.20 g, 1.0 equiv.) was added to 20 C. The resultingmixture was warmed to 20 C in 0.5 h and quenched with water (6 mL). After stirring the mixturebelow 20 C for 10 min, the phases were separated and the water phase was extracted one additionaltime with ethyl acetate. The resulting suspension was allowed to reach room temperature and ®teredthrough a 0.5 1 cm pad of silica gel eluted with 10 mL of ethyl acetate. The ®ltrate was concentratedand the residue was puri®ed by ash chromatography on silica gel (eluent: petroleum ether/ethylacetate = 3:1) to afford product 3f as brown solid, 0.68 g (yield: 80percent), m.p.: 199–201 C. 1H-NMR(600 MHz, DMSO) 7.36 (d, J = 8.9 Hz, 1H), 7.06 (d, J = 23.6 Hz, 2H), 6.90 (d, J = 8.8 Hz, 1H), 3.73 (s, 3H).13C-NMR (151 MHz, DMSO) 163.25, 154.31, 133.07, 129.10, 127.65, 116.28, 113.83, 107.47, 102.44, 55.61.

Reactant for preparation of:• ;Anticancer agents1• ;A fluorescent small molecule probe for in vivo lipid imaging2• ;Indoleamine 2,3-dioxygenase (IDO) inhibitors3• ;Selective Dopamine D3 receptor ligands4• ;5-HT4 receptor ligands5• ;Inhibitors of Mycobacterium tuberculosis pantothenate synthetase6• ;Hypoxia selective cytotoxins7• ;Potent antitumor bifunctional DNA alkylating agents8

Molecular Weight:191.18
XLogP3:2.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:191.058243149
Monoisotopic Mass:191.058243149
Topological Polar Surface Area:62.3
Heavy Atom Count:14
Complexity:231
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes