I[C:2]1[N:3]=[CH:4][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1.C([Mg]Br)C.CN[C:32](=O)[C:33]1[CH:38]=[CH:37][CH:36]=[N:35][C:34]=1[CH3:39].[Cl-:41].[NH4+]>ClCCl.C(OCC)C>[ClH:41].[ClH:41].[CH3:39][C:34]1[C:33]([CH2:32][C:2]2[N:3]=[CH:4][NH:5][CH:6]=2)=[CH:38][CH:37]=[CH:36][N:35]=1
To a solution of 4-iodo-1-tritylimidazole (6.88 g, 15.8 mmol) in 65 mL anhydrous dichloromethane was added 6.3 mL of a solution of ethyl magnesium bromide (3.0 M, 18.9 mmol) in diethyl ether under argon. The reaction mixture was stirred for 2.5 h, and then a solution of N-methoxy, N-methyl-2-methylnicotinamide (2.84 g, 15.8 mmol) was added. After 5 days of stirring, the reaction mixture was poured into saturated aqueous ammonium chloride solution (125 mL). The layers were separated, and the aqueous layer was extracted twice with dichloromethane (50 mL). The organic extracts were combined, dried (Na2SO4), and concentrated to provide a red-orange foam which was purified on flash silica gel (1% methanol-chloroform to 2% methanol-chloroform) to provide the desired product as 5.56 g (82%) of a golden-brown foam. MS (PB-NH3), m/z 430 (MH+). 1H NMR (CDCl3) δ 2.63 (s, 3H), 7.02-7.16 (m, 7H), 7.19 (dd, J=7.8, 5.1 Hz, 1H), 7.28-7.41 (m, 8H), 7.49 (d, J=0.9 Hz, 1H), 7.70 (d, J=0.9 Hz, 1H), 7.96 (dd, J=7.9, 1.2 Hz, 1H), 8.57 (dd, J=7.9, 4.9 Hz, 1H.
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