Sodium Hydroxide → 4-bromo-N-(4-methoxybenzyl)picolinamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	4-Methoxybenzylamine	HCID 75452	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Bromopyridine-2-carboxylic acid	HCID 735150	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-bromo-N-(4-methoxybenzyl)picolinamide	HCID 70978467	75.5%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a flask containing a 4-bromopicolinic acid (1.0 g) in DMF (10 mL) was added HATU (2.3 g) and N-ethyl-N-isopropylpropan-2-amine (1.0 mL) The mixture was stirred at about 25° C. for approximately 10 min followed by addition of (4-methoxyphenyl)methanamine (0.68 g). The reaction was then stirred at about 25° C. for about an additional 12 h. The reaction was basified to pH 10 with aqueous 1 N NaOH and washed three times with EtOAc. The organic solution was dried over MgSO4, filtered, and concentrated under reduced pressure to afford 4-bromo-N-(4-methoxybenzyl)picolinamide as a clear oil (1.2 g, 75%). LC/MS (Table 1, method f). Rt=1.73 min; MS m/z 322 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09029409B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-297c5b2b9d2e46d6b34961d6760b7803
Source note	uspto-grants-2015_05