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0 °C

To a stirred suspension of NaH (102 mg of an 807. dispersion, 3.39 mmol) in dry dimethylformamide (6 mL) at rt was added 2-butylimidazo[4,5-b]pyridine (495 rag, 2.83 mmol) in one portion. After 20 minutes, the mixture was cooled to 0° C. and N-triphenylmethyl-5-(4'-bromomethylbiphenyl-2-yl)-tetrazole (1.50 g, 2.70 mmol) was added in one portion. The resulting dark colored mixture was warmed to rt and stirred for 15 hours. The excess Nail was quenched with water (1 mL) and the bulk of the DMF was removed in vacuo at 40°-50° C. Extraction with EtOAc (4×20 mL) from brine (60 mL), drying (K2CO3), and concentration gave a thick dark oil. Purification by flash chromatography (SiO2, solvent gradient: 80% EtOAc/hexanes, 100% EtOAc) gave 417 mg (23%) of 2-butyl-3-(2'-(N-triphenylmethyltetrazol-5-yl)biphen-4-yl)methyl-1H-imidazo[ 4,5-b ]pyridine as a thick oil: Rf=0.75 (SiO2, 100% EtOAc), 1H NMR (300 MHz, CDCl3) δ 8.35 (1H, dd, J=6, 1 Hz), 8.05 (1H, dd, J=9, 1 Hz), 7.92 (1H, dd, J=9, 1.5 Hz), 7.51-7.42 (3H, m), 7.36-7.20 (11 H, M), 7.07 (2H, d, 7 Hz), 6.96-6.89 (7H, m), 5.40 (2H, s), 2.73 (2H, t, J=7.5 Hz), 1.84-1.70 (2H, m), 1.41-1.30 (2H, m), 0.88 (3H, t, J=7.5 Hz).

1. temperatureThe resulting dark colored mixture was warmed to rt
2. customThe excess Nail was quenched with water (1 mL)
3. customthe bulk of the DMF was removed in vacuo at 40°-50° C
4. extractionExtraction with EtOAc (4×20 mL) from brine (60 mL)
5. customdrying
6. concentration(K2CO3), and concentration
7. customgave a thick dark oil
8. customPurification by flash chromatography (SiO2, solvent gradient: 80% EtOAc/hexanes, 100% EtOAc)