2-Bromo-6-methoxypyridine → HCID 86602989, compound

HRID 2099566Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.[Li]CCCC.[Br:15][C:16]1[N:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][CH:17]=1>C1COCC1>[Br:15][C:16]1[N:21]=[C:20]([CH:22]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=2)[OH:23])[CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2-bromo-6-methoxy-pyridine (5.00 g, 26.59 mmol) in anhydrous THF (100 mL) @ −78° C. under N2 was added n-BuLi (11.701 mL, 2.5 M) dropwise. The mixture was stirred for 20 min and 6-Bromo-2-pyridine carboxaldehyde (4.95 g, 26.93 mmol was added. The mixture was warmed to 0° C. and stirred for 1 hr. The resulting mixture was quenched with saturated aqueous NH4Cl, and extracted 3× with EtOAc. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (15% EtOAc in hexanes) to give (6-bromopyridin-2-yl)(6-methoxypyridin-2-yl)methanol. 1H NMR (500 MHz, CDCl3) δ 7.60-7.49 (m, 3H), 7.37 (dd, 1H, J=7.1, 1.5), 7.12 (d, 1H, J=7.3), 6.64 (d, 1H, J=8.3), 5.78 (d, 1H, J=5.4), 5.27 (d, 1H, J=5.4), 3.97 (s, 3H), LRMS m/z, (M+H) Calcd.: 295.0, found 295.1.

Workup

custom@ −78° C. under N2
stirringstirred for 1 hr
customThe resulting mixture was quenched with saturated aqueous NH4Cl
extractionextracted 3× with EtOAc
dry with materialThe combined organics were dried (anhd. Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (15% EtOAc in hexanes)

Sources & evidence

ORD record: ord-a95ec5a72edf4f67b028f8d844c5fef2
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569589B2

Reaction notes

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