Sodium hydride → HCID 58335249, compound

HRID 1504786Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[N:5]=1.[C:12]([O:16][CH3:17])(=[O:15])[CH2:13][OH:14]>CN(C=O)C>[Br:3][C:4]1[N:5]=[C:6]([CH2:10][O:14][CH2:13][C:12]([O:16][CH3:17])=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of sodium hydride (60% in mineral oil, 72 mg, 1.8 mmol) in DMF (3.30 mL) at 0° C. was added dropwise a mixture of 2-bromo-6-(bromomethyl)pyridine (493 mg, 1.97 mmol) and methyl glycolate (148 mg, 1.64 mmol) in DMF (1.5 mL), and the reaction mixture was stirred for 2 hours at 0° C. The reaction mixture was quenched with 1:1 isopropanol:methanol (5 mL) and then poured over ice. The reaction mixture was diluted with water and diethyl ether. The organics were separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford methyl [(6-bromopyridin-2-yl)methoxy]acetate. MS ESI calc'd. for C9H11BrNO3 [M+H]+ 260 and 262. found 260 and 262. 1H NMR (500 MHz, CDCl3) δ 7.58 (t, J=7.7 Hz, 1H), 7.49 (d, J=7.5 Hz, 1H), 7.40 (d, J=7.8 Hz, 1H), 4.72 (s, 2H), 4.23 (s, 2H), 3.78 (s, 3H).

Workup

additionwas added dropwise
customThe reaction mixture was quenched with 1:1 isopropanol
additionmethanol (5 mL) and then poured over ice
additionThe reaction mixture was diluted with water and diethyl ether
customThe organics were separated
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-4b2391cff86947f0a8df4964548e2a95
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

Loading…