Anes (5 mL) and with water (five mL). The aqueous layer was extracted
Anes (five mL) and with water (5 mL). The aqueous layer was extracted 3 times with ethyl acetate (20 mL), along with the combined JAK2 Storage & Stability organic layers were washed with brine (ten mL) and dried over anhydrous Na2SO4. Solvent evaporation below lowered stress afforded compound 8 as a brown oil (0.114 g, 0.241 mmol, 90 ), which was applied directly inside the next step without further purification.dx.doi.org10.1021ic5008439 | Inorg. Chem. 2014, 53, 7518-ArticleEXPERIMENTAL SECTIONInorganic Chemistry(Note that to be able to get the preferred compound in high yields and free of side goods, this reaction couldn’t be performed on much more than 0.150 g of 7.) 1H NMR (500 MHz, CDCl3, ): 8.79 (s, 1H), 7.82 (s, 1H), 7.40-7.32 (m, 3H), 7.24-7.20 (m, 2H), six.87 (dd, J = three.7, 2.5 Hz, 1H), 6.11 (dd, J = three.six, two.7 Hz, 1H), six.01 (ddd, J = three.six, two.7, 0.7 Hz, 1H), five.88 (ddd, J = 3.7, two.five, 0.9 Hz, 1H), five.44 (s, 1H), four.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 mz (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). Compound eight (0.114 g, 0.241 mmol) was dissolved in THF (6.7 mL) at 0 . two,3-Dichloro-5,6dicyano-1,4-benzoquinone (DDQ, 55 mg, 0.241 mmol) was dissolved in THF (1.4 mL) and added dropwise. 1,5-Diazabicyclo(4.three.0)non-5ene (DBN, 30 L, 0.241 mmol) was added, along with the mixture was stirred at room temperature for 7 h. The reaction mixture was quenched by adding saturated aqueous NaHCO3 (ten mL), along with the aqueous layer was extracted three times with CH2Cl2 (ten mL). The combined organic layers have been washed with brine (ten mL) and dried more than anhydrous Na2SO4. Solvent evaporation under reduced stress resulted in a brown oil. The crude item was redissolved in 1:1 mixture of ethyl acetatehexanes and filtered through a silica pad in an effort 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), six.87 (dd, J = 4.1, two.four Hz, 1H), six.76 (d, J = 4.5 Hz, 1H), 6.52 (d, J = 4.5 Hz, 1H), 6.33 (dd, J = 4.1, two.four Hz, 1H), four.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 mz (relative intensity): 370.9 (19 ), 325.1 (100 ). (Z)-Ethyl 5-[1H,5H(2,2-Bipyrrol]-5-ylidene(phenyl)methyl]1H-pyrrole-2-carboxylate (H2PD1). Compound 9 (75 mg, 0.202 mmol), LiCl (30 mg, 0.707 mmol), pyrrole-2-boronic acid (64 mg, 0.303 mmol), and Pd(PPh3)four (23 mg, 10 mol , 20.two mol) were dissolved in 1,2-dimethoxyethane (six.1 mL), and the GLUT3 Gene ID answer was degassed for two h. A degassed option of aqueous Na2CO3 (two M, 0.5 mL) was added dropwise, and the mixture was refluxed for 2 h. The reaction mixture was cooled to room temperature and diluted with water (10 mL). The aqueous layer was extracted 3 instances with CH2Cl2 (ten mL). The combined organic layers had been washed with brine (10 mL) and dried more than anhydrous Na2SO4. Solvent evaporation under reduced pressure afforded the crude product, which was dissolved in CH2Cl2 (10 mL). The solution was cooled to 0 , and trifluoroacetic acid (0.eight mL) was added dropwise. The mixture was stirred at room temperature for 8 h, cooled to 0 , and carefully quenched with saturated aqueous NaHCO3 (20 mL). The mixture was extracted three times with CH.