METHYL4-BROMO-1-METHYL-1H-PYRROLE-2-CARBOXYLATE

To a stirred solution of 1-(4-bromo-1-methyl-1 H-pyrrol-2-yl)-2, 2, 2-trichloro-ethanone (3)(3.28 g, 10.74 mmol, 1 eq.) in dry MeOH (30 mL), a solution of sodium methoxide (0.5 mL) was added by a syringe. The sodium methoxide solution was prepared from NaH 60percent in mineral oil (43 mg, 1.07 mmol, 0.1 eq.), which was previously washed with n- hexane. The solution was heated to reflux over a period of 30 minutes, when the TLC analysis showed complete consumption of the starting material. A few drops of concentrated HTo a stirred solution of 1-(4-bromo-1-methyl-1 H-pyrrol-2-yl)-2, 2, 2-trichloro-ethanone (3)(3.28 g, 10.74 mmol, 1 eq.) in dry MeOH (30 mL), a solution of sodium methoxide (0.5 mL) was added by a syringe. The sodium methoxide solution was prepared from NaH 60percent in mineral oil (43 mg, 1.07 mmol, 0.1 eq.), which was previously washed with n- hexane. The solution was heated to reflux over a period of 30 minutes, when the TLC analysis showed complete consumption of the starting material. A few drops of concentrated HTo a solution of 10 (3.1 g, 10 mmol) in dry MeOH (50 mL) was added sodium methoxide (0.81 g, 15 mmol) in several portions at 0 °C. The resulting mixture was stirred at r.t. for 1 h, and quenched with HCl (1N, 5 ml). The solvent was evaporated, and the crude residue was extracted with ethyl acetate and washed with brine. The organics were dried over anhydrous NaTo a stirred solution of 1-(4-Bromo-1-methyl-lH-pyrrol-2-yl)- 2, 2, 2-trichloro-ethanone (3.28 g, 10.74 mmol, 1 Equiv. ) in dry MeOH (30 mL) was added through a syringe a solution of sodium methoxide (0.5 mL). The sodium methoxide solution was prepared from NaH 60percent in mineral oil (43 mg, 1.07 mmol, 0.1 Equiv. ), which was previously washed with hexane. The solution was heated to reflux over a period of 30 minutes, when the TLC analysis showed complete consumption of the starting material. Few drops of concentrated H2SO4 were added to the solution to neutralise the base (pH 2). The excess MeOH was evaporated in vacuum and the resulting oil was redissolved in EtOAc (50 mL) and washed with water (40 mL). The aqueous layer was extracted with EtOAc (3 x 40 mL), and the organic phases were combined, dried (MgSO4), filtered and concentrated in vacuum to afford the product 30 as a pale solid. (2.28 g, 97percent) IR (film, cm~1) 3138, 2948, 1692 (C=O), 1472, 1435, 1389, 1334, 1245, 1197, 1115, 1082, 1062, 921, 823, 807, 753; 1H NMR (CDC13) 8 6.89 (1H, d, J = 1.97Hz, H-3), 6.76 (1H, d, J = 1.93Hz, H-5), 3.89 (3H, s, NCH3), 3.81 (3H, s, OCH3) ; 13C NMR (CDCl3) 8 160.8 (C=O), 128.7 (C5), 122.9 (C2), 119.2 (C3), 95.1 (C4), 51.2 (OCH3) 36.9 (CH3).NaH (256 mg, 6.40 mmol) was added into DMF (5 mL) and stirred at 0 °C under nitrogen for 10 min. A solution of 4-bromo-lH-pyrrole-2-carboxylic acid methyl ester (1 g, 4.93 mmol) in DMF (5 mL) was added in 15 min at 0 °C. The resulting mixture was stirred at 0°C for 30 min. Mel (909 mg, 6.40 mmol) was added to the reaction mixture. After being stirred for another 18 h at room temperature, the mixture was poured into water, and then extracted with MTBE twice. The combined organic layers were washed with brine, and then dried over anhydrous Na

Molecular Weight:218.05
XLogP3:1.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:216.97384
Monoisotopic Mass:216.97384
Topological Polar Surface Area:31.2
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes