2-(Hydroxymethyl)-1H-benzimidazole → HCID 69295003, compound

Temperature

60 °C

To a solution of (bromomethyl)cyclopropane (0.39 mL, 4.02 mmol) and (1H-benzoimidazol-2-yl)-methanol (596 mg, 4.02 mmol) in DMF (10 mL) was added N,N-diisopropylethylamine (0.84 mL, 4.82 mmol). The reaction mixture was stirred at 60° C. for 3 days. Then it was cooled to room temperature and quenched with saturated NaHCO3 (15 mL) and the phases were separated. The aqueous phase was washed with CH2Cl2 (3×20 mL). Then the combined organic layers were washed with brine (2×30 mL), dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a dark brown oil. Purification by flash column chromatography on silica gel using 2% CH3OH/CH2Cl2 afforded the product as a yellow solid (210 mg, 26%). 1H NMR (CDCl3) δ 0.40-0.45 (m, 2H), 0.52-0.61 (m, 2H), 1.22-1.33 (m, 1H), 4.13 (d, 2H, J=6.6 Hz), 4.88 (s, 2H), 7.22-7.24 (m, 2H), 7.36-7.38 (m, 1H), 7.66-7.69 (m, 1H).

1. temperatureThen it was cooled to room temperature
2. customquenched with saturated NaHCO3 (15 mL)
3. customthe phases were separated
4. washThe aqueous phase was washed with CH2Cl2 (3×20 mL)
5. washThen the combined organic layers were washed with brine (2×30 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customdried in vacuo
10. customto afford a dark brown oil
11. customPurification by flash column chromatography on silica gel using 2% CH3OH/CH2Cl2

ORD record

ord-233b25b5575e4ac694bb3ab0eed68b41

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354932B2