Ssure (to remove the acetic acid), the crude compound was purified by flash chromatography (silica gel, 25 ethyl acetate in hexanes) to yield 7 as an orange-brown oil (1.27 g, 4.33 mmol, 72 ). 1H NMR (500 MHz, CDCl3, ): eight.84 (s, 1H), 7.92 (s, 1H), 7.39-7.30 (m, 3H), 7.25-7.21 (m, 2H), six.88 (dd, J = 3.7, two.5 Hz, 1H), six.75 (ddd, J = two.7, 1.6, 0.7 Hz, 1H), six.20 (dd, J = six.1, 2.7 Hz, 1H), 6.00 (ddd, J = 3.6, 2.7, 0.7 Hz, 1H), 5.97 (dddd, J = 3.7, two.5, 1.6, 0.9 Hz, 1H), five.51 (s, 1H), 4.30 (q, J = 7.1 Hz, 2H), 1.36 (t, J = 7.1 Hz, 3H). 13C NMR (125 MHz, CDCl3, ): 161.11, 140.83, 138.15, 131.08, 128.88, 128.31, 127.30, 122.15, 117.74, 115.54, 109.82, 108.56, 107.74, 60.27, 44.16, 14.94. LRMS-ESI+ m/z (relative intensity): 294.0 (4 ), 228.0 (100 ). Ethyl 5-[(5-Bromo-1H-pyrrol-2-yl)(phenyl)methyl]-1H-pyrrole-2-carboxylate (8). Compound 7 (0.one hundred g, 0.340 mmol) was dissolved in THF (6 mL) at -78 . N-Bromosuccinimide (61 mg, 0.340 mmol) was added for the reaction flask in one particular portion, plus the mixture was stirred at -78 for 30 min. The reaction mixture was diluted with hexanes (five mL) and with water (5 mL).4,6-Dichloro-2-(ethoxymethyl)pyrimidine In stock The aqueous layer was extracted 3 instances with ethyl acetate (20 mL), along with the combined organic layers have been washed with brine (ten mL) and dried over anhydrous Na2SO4. Solvent evaporation below decreased stress afforded compound 8 as a brown oil (0.114 g, 0.241 mmol, 90 ), which was applied straight within the next step devoid of additional purification.dx.doi.org/10.1021/ic5008439 | Inorg. Chem. 2014, 53, 7518-ArticleEXPERIMENTAL SECTIONInorganic Chemistry(Note that to be able to receive the desired compound in higher yields and cost-free of side items, this reaction could not be conducted on far more than 0.150 g of 7.) 1H NMR (500 MHz, CDCl3, ): eight.79 (s, 1H), 7.82 (s, 1H), 7.40-7.32 (m, 3H), 7.24-7.20 (m, 2H), 6.87 (dd, J = 3.7, two.5 Hz, 1H), six.11 (dd, J = three.six, two.7 Hz, 1H), six.01 (ddd, J = three.six, two.7, 0.7 Hz, 1H), five.88 (ddd, J = three.7, two.five, 0.9 Hz, 1H), five.44 (s, 1H), 4.31 (q, J = 7.1 Hz, 2H), 1.36 (t, J = 7.1 Hz, 3H). 13C NMR (125 MHz, CDCl3, ): 161.71, 140.36, 137.84, 132.19, 128.65, 128.14, 127.34, 122.29, 116.01, 110.47, 109.97, 109.45, 97.54, 60.47, 44.21, 14.35. LRMS-ESI+ m/z (relative intensity): 372.1 (33 ), 327.0 (one hundred ). (Z)-Ethyl 5-[(5-Bromo-2H-pyrrol-2-ylidene)(phenyl)methyl]1H-pyrrole-2-carboxylate (9).138517-61-0 structure Compound 8 (0.PMID:24633055 114 g, 0.241 mmol) was dissolved in THF (six.7 mL) at 0 . 2,3-Dichloro-5,6dicyano-1,4-benzoquinone (DDQ, 55 mg, 0.241 mmol) was dissolved in THF (1.four mL) and added dropwise. 1,5-Diazabicyclo(four.3.0)non-5ene (DBN, 30 L, 0.241 mmol) was added, along with the mixture was stirred at area temperature for 7 h. The reaction mixture was quenched by adding saturated aqueous NaHCO3 (ten mL), along with the aqueous layer was extracted three occasions with CH2Cl2 (10 mL). The combined organic layers had been washed with brine (ten mL) and dried more than anhydrous Na2SO4. Solvent evaporation below reduced stress resulted within a brown oil. The crude solution was redissolved in 1:1 mixture of ethyl acetate/hexanes and filtered by way of a silica pad so as to give compound 9 (75 mg, 0.202 mmol, 84 ) as a yellow oil. 1 H NMR (500 MHz, CDCl3, ): 7.55-7.45 (m, 5H), 6.87 (dd, J = 4.1, 2.4 Hz, 1H), 6.76 (d, J = 4.five Hz, 1H), six.52 (d, J = four.5 Hz, 1H), six.33 (dd, J = four.1, 2.4 Hz, 1H), 4.43 (q, J = 7.1 Hz, 2H), 1.46 (t, J = 7.1 Hz, 3H). 13C NMR (125 MHz, CDCl3, ): 160.54, 150.17, 149.00, 139.47, 137.00, 135.65, 134.87, 130.65, 129.57, 128.39, 127.99, 121.63, 115.54, 60.76, 14.26. LRMS-ESI+ m/z (relati.
