Bis(2-bromoethyl) ether → HCID 90408923, compound

Temperature

120 °C

To a solution of 5-bromo-6-methoxypyridin-3-amine (1.0 equiv.) in DMF was added DIEA (3.0 equiv.) and 1-bromo-2-(2-bromoethoxy)ethane (1.0 equiv.). The solution was heated to 120° C. for 24 hours. Upon cooling to room temperature, the reaction was partitioned between water and ethyl acetate, the aqueous phase was extracted three times with ethyl acetate, the organics were combined, dried with sodium sulfate, filtered and concentrated. The crude material was purified via silica gel column chromatography eluting with 0-50% ethyl acetate in heptanes. The pure fractions were concentrated to yield 4-(5-bromo-6-methoxypyridin-3-yl)morpholine in 53% yield as an orange oil. LCMS m/z (M+H)=273/275, Rt=0.61 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 2.93-3.18 (m, 4H) 3.80-4.05 (m, 7H) 7.50 (d, J=2.74 Hz, 1H) 7.74 (d, J=2.74 Hz, 1H).

1. temperatureUpon cooling to room temperature
2. customthe reaction was partitioned between water and ethyl acetate
3. extractionthe aqueous phase was extracted three times with ethyl acetate
4. dry with materialdried with sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude material was purified via silica gel column chromatography
8. washeluting with 0-50% ethyl acetate in heptanes
9. concentrationThe pure fractions were concentrated

ORD record

ord-3db7b13d973945f6bfb8c5e4e25cec64

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242969B2