Diisopropylethylamine → 5-bromo-N-((2'-fluoro-2,4'-bipyridin-5-yl)methyl)picolinamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	5-Bromopyridine-2-carboxylic acid	HCID 608544	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	(2'-Fluoro-2,4'-bipyridin-5-yl)methanamine	HCID 67208618	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	5-bromo-N-((2'-fluoro-2,4'-bipyridin-5-yl)methyl)picolinamide	HCID 67208643	—

Reaction Steps

To a mixture of 5-bromopicolinic acid 38-3 (309 mg, 1.53 mmol), (2′-fluoro-2,4′-bipyridin-5-yl)methanamine 38-2 (312 mg, 1.53 mmol) and HATU (582 mg, 1.53 mmol) in DMF (7 mL) was added DIEA (0.76 mL, 4.59 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (100 mL), washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 5% methanol containing ˜7N ammonia in dichloromethane to give 5-bromo-N-((2′-fluoro-2,4′-bipyridin-5-yl)methyl)picolinamide 38-4 as yellow solid. MS m/z 387.1 (M+1)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181235B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-281196e8c3e24064933e183167d3829a
Source note	uspto-grants-2015_11