Methylamine → HCID 86694278, compound

2-Amino-3-bromo-5-fluoropyridine (1.127 g, 5.90 mmol) and BrettPhos Precatalyst (0.141 g, 0.177 mmol) were mixed under an argon atmosphere. Methylamine (2.0 M in THF, 4.43 ml, 8.85 mmol) and lithium bis(trimethylsilyl)amide (1.0 M in THF, 14.75 ml, 14.75 mmol) were added slowly via syringe, and the reaction mixture was stirred at room temperature for 3.5 h. The reaction mixture was quenched with saturated aqueous ammonium chloride and extracted three times with a 9:1 mixture of DCM to MeOH. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with acetone in DCM to yield the title compound (0.497 g, 3.52 mmol, 59.7% yield) as a tan solid. M+1: 142.1.

1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
2. extractionextracted three times
3. additionwith a 9:1 mixture of DCM to MeOH
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting crude product was purified by silica gel column chromatography
8. washeluting with acetone in DCM

ORD record

ord-e0cd5f60cb2147e5955d8cba9e9375ae

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174992B2