D with brine, dried more than MgSO4, and filtered. The filtrate was concentrated and purified by flash column chromatography (SiO2, 7 g, 25 EtOAc/ hexanes) to offer the terminal acetylene 23 as a white solid (0.092 g, 68 yield): TLC Rf = 0.1 (25 EtOAc/hexanes); mp 113.6-115.three ; 1H NMR (500 MHz, CDCl3) 7.61 (d, J = 7.eight Hz, 1H), 7.56 (d, J = eight.five Hz, 2H), 7.19 (d, J = 8.5 Hz, 2H), 7.15 (dd, J = 7.8, 1.4 Hz, 1H), 7.01 (d, J = 1.7 Hz, 1H), 4.21 (qd, J = 7.0, 2.3 Hz, 1H), three.88 (s, 3H), 2.23 (d, J = two.four Hz, 1H), 1.47 (d, J = 7.0 Hz, 3H); 13C NMR (125 MHz, CDCl3) 189.two, 156.4, 155.six, 150.3, 140.6, 138.9, 133.1, 130.3, 128.3, 128.2, 122.1, 119.7, 109.six, 87.7, 69.six, 60.six, 55.7, 25.3, 22.8, 21.two, 14.four; IR (neat cm-1) 3423, 3308, 3268, 3199, 2969, 2341, 2105, 1698, 1606, 1494, 1378, 1213, 586; HRMS (DART, M+ + H) m/z 296.1300 (calculated for C18H18NO3, 296.1287). 3-Methoxy-4-(1-methyl-prop-2-ynyl)-biphenyl-4-carboxylic Acid Methyl Ester (24). In line with the general procedure for homologation, methoxymethyl triphenylphosphonium chloride (1.05 g, 3.06 mmol) in dry THF (9 mL), NaOtBu (0.367 g, 3.9 mmol), and ketone 14 (0.434 g, 1.59 mmol) in THF (three mL) have been Monoamine Oxidase Inhibitor web stirred at 0 . Following the common workup, the mixture of enol ethers (0.214 g, 0.69 mmol) in THF/H2O (9:1, 5 mL) was hydrolyzed using Hg(OAc)2 (0.656 g, 2.1 mmol) at room temperature. Just after the basic TLR7 Purity & Documentation extraction process, aldehyde (0.194 g, 0.65 mmol) in MeOH (3 mL), the Ohira-Bestmann reagent (0.224 g, 1.17 mmol) dissolved in MeOH (two mL), and powdered K2CO3 (0.188 g, 1.36 mmol) have been stirred at 0 . Following the basic workup and flash chromatography (SiO2, 7 g, 2 EtOAc/hexanes), alkyne 24 was obtained as a white solid (0.111 g, 25 yield more than 3 methods); TLC Rf = 0.three (5 EtOAc/hexanes); mp 106-108.5 ; 1H NMR (500 MHz, CDCl3) eight.09 (d, J = 8.1 Hz, 2H), 7.72-7.57 (m, 3H), 7.20 (d, J = 7.7 Hz, 1H), 7.06 (s, 1H), 4.21 (q, J = five.0 Hz, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 2.23 (d, J = 2.0 Hz, 1H), 1.47 (d, J = 7.0 Hz, 3H); 13C NMR (125 MHz, CDCl3) 167.1, 156.five, 145.eight, 140.1, 131.3, 130.two, 129.1, 128.four, 127.2, 119.9, 109.five, 87.5, 69.7, 55.7, 52.three, 25.four, 22.8; IR (neat cm-1)3255, 2970, 2950, 2929, 2108, 1698, 1605, 1430, 1393, 1104, 1281, 769, 676; HRMS (DART, M+ + H) m/z 295.1329 (calculated for C19H19O3, 295.1334). 3-Methoxy-4-(1-methyl-prop-2-ynyl)-biphenyl-4-yl)-dimethylamine (25). According to the general process for homologation, methoxymethyl triphenylphosphonium chloride (0.67 g, 1.95 mmol) in dry THF (10 mL), NaOtBu (0.22 g, 2.34 mmol), and ketone (0.21 g, 0.78 mmol) in THF (three mL) were stirred at 0 . Following the common workup, the mixture of enol ethers (0.18 g, 0.62 mmol) in THF/H2O (9:1, ten mL) was hydrolyzed employing Hg(OAc)two (0.30 g, 0.93 mmol) at area temperature. Following the common extraction process, aldehyde (0.17 g, 0.62 mmol) in dry MeOH (six mL), theArticleOhira-Bestmann reagent (0.36 g, 1.86 mmol) dissolved in MeOH (2 mL), and powdered K2CO3 (0.26 g, 1.86 mmol) have been stirred at 0 . Following the common workup and flash chromatography (SiO2, 10g, 15 EtOAc/hexanes), alkyne 25 was obtained as a white strong (0.015 g, 6 yield more than three methods); TLC Rf = 0.52 (ten EtOAc/hexanes); mp 60.8- 61.1 ; 1H NMR (500 MHz, chloroform-d) 7.56 (d, J = 7.9 Hz, 1H), 7.48 (d, J = 8.9 Hz, 2H), 7.14 (dd, J = 7.9, 1.7 Hz, 1H), 7.01 (d, J = 1.6 Hz, 1H), 6.79 (d, J = 8.7 Hz, 2H), 4.18 (qd, J = 7.1, 2.6 Hz, 2H), 3.88 (s, 3H), two.98 (s, 6H), 2.20 (d, J = two.5 Hz, 1H), 1.46 (d, J = 7.1 Hz, 3H); 13C NMR (12.