Boron tribromide → 4-[3-(4-Chloro-phenyl)-5,6,7,8-tetrahydro-4H-1,2,6-triaza-azulen-1-ylmethyl]-2-fluoro-phenol

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Reaction Steps

BBr3 (0.13 mL) was added slowly to a 0° C. solution of 0.022 g of 3-(4-chloro-phenyl)-1-(3-fluoro-4-methoxy-benzyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene (Example 96) in CH2Cl2 (20 mL). After 1 h, the mixture was warmed to RT and stirred for 18 h. The reaction was then cooled back to 0° C. and quenched by the addition of 5 mL of satd. aq. NaHCO3. The aqueous layer was extracted with methanolic CH2Cl2 (2×). The combined organic layers were dried over Na2SO4 and concentrated. The crude oil was purified by preparative TLC (9:1 CH2Cl2/2 M NH3 in MeOH) to afford the title compound (0.016 g) as a tan solid. MS (ESI): exact mass calculated for C20H19ClFN3O, 371.12; found, m/z 372.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.50-7.42 (m, 4H), 6.86-6.79 (m, 3H), 5.26 (s, 2H), 3.31-3.26 (m, 2H), 2.96-2.95 (m, 4H), 2.90-2.87 (m, 2H), 2.81-2.79 (m, 2H). 13C NMR (100 MHz, CD3OD): 154.2, 151.8, 149.6, 146.1, 146.0, 143.8, 134.8, 133.4, 131.1, 130.3, 130.2, 129.7, 124.0, 119.1, 115.6, 115.4, 53.1, 50.4, 29.0, 27.5.

Provenance & Evidence