Hydrochloric Acid → HCID 58763629, compound

Temperature

0 °C

(6-Chloro-8-methyl-2-phenyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid 43a (239 mg, 0.80 mmol) was suspended in anhydrous THF (3 mL) and cooled to 0° C. A borane solution (BH3.THF) (1.0 M in THF, 2.4 mL, 2.4 mmol) was added, and the resulting opaque solution was stirred at a temperature ranging from about 0° C. to about room temperature over 4 h. All material was in solution after about 1 h. 2 M HCl (5 mL) was added slowly, and the resulting solution was allowed to stir at room temperature for 1 h, then washed with CH2Cl2 (3×20 mL). The organic washes were combined and washed with brine (1×20 mL), then dried (Na2SO4), filtered and concentrated to give the title compound (209 mg, 92%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=1.1 Hz, 1H), 7.55-7.53 (m, 2H), 7.35-7.33 (m, 2H), 6.79 (s, 1H), 3.82 (t, J=5.87 Hz, 2H), 2.99 (at, 2H), 2.49 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 143.1, 142.9, 128.7, 128.5, 127.9, 127.3, 124.8, 120.2, 120.1, 61.8, 27.8, 16.9. Mass spectrum (m/e) 286 (M+).

1. waitAll material was in solution after about 1 h
2. stirringto stir at room temperature for 1 h
3. washwashed with CH2Cl2 (3×20 mL)
4. washwashed with brine (1×20 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-48f119ebe9a1439784c23cfdbc0772f4

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723324B2