Tetrahydrofuran → HCID 59825022, compound

Temperature

0 °C

3,5-Dibromo-pyridine (1 g, 4.22 mmol) was dissolved in 5 mL of tetrahydrofuran and cooled to 0° C. A solution of isopropyl magnesium lithium chloride (15% in tetrahydrofuran, 5.07 mL, 5.06 mmol) was added dropwise and the solution was stirred for 15 min at 0° C. The resulting solution was added to a solution of cyclopropyl aldehyde (0.31 mL, 4.22 mmol) in 2 mL of tetrahydrofuran at 0° C. and the mixture was stirred for another 30 min at 0° C. The reaction was quenched with a saturated solution of ammonium chloride (10 mL) and water (10 mL). The crude mixture was passed through a Varian Chemelut cartridge (ethyl acetate as eluent) and concentrated to afford 623 mg of (5-Bromo-pyridin-3-yl)-cyclopropyl-methanol as an oil (2.73 mmol, 65% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.57 (m, 2H), 7.99 (t, J=2 Hz, 1H), 5.49 (d, J=5 Hz, 1H), 4.02 (m, 1H), 1.04 (m, 1H), 0.47 (m, 1H), 0.4 (m, 3H). MS: m/z 228.0/230.0 (M+H+).

1. stirringthe mixture was stirred for another 30 min at 0° C
2. customThe reaction was quenched with a saturated solution of ammonium chloride (10 mL) and water (10 mL)
3. concentrationconcentrated

ORD record

ord-d86fadf8657f4ceba379f340eecc9772

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242280B2