Dimethylformamide → N-Methyl-2-(6-methylaminopyridin-3-yl)benzothiazol-6-amine

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine	HCID 2756555	—
Reactant	2-Bromo-6-((tert-butyldimethylsilyl)oxy)benzo[d]thiazole	HCID 57553400	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	N-Methyl-2-(6-methylaminopyridin-3-yl)benzothiazol-6-amine	HCID 24804556	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 2-bromo-6-{[tert-butyl(dimethyl)silyl]oxy}-1,3-benzothiazole (500 mg, 1.45 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (383 mg, 1.2 equiv), aqueous potassium carbonate (2.0 M, 2.9 ml, 4.0 equiv) and Pd(dppf)Cl2 (119 mg, 0.10 equiv) in DMF (6.0 ml) was stirred at 80° C. under argon for 2 h. The mixture was then added to DCM (100 ml), dried (Na2SO4) and concentrated in vacuo. The crude thus obtained was purified by silica gel chromatography by gradient elution (n-heptane:ethyl acetate) to yield 237 mg of the title compound. 1H NMR δ 9.74 (s, 1H) 8.53 (d, 1H) 7.94 (dd, 1H) 7.73 (d, 1H) 7.35 (d, 1H) 6.93 (dd, 1H) 6.61 (s, 2H) 6.55 (d, 1H); MS m/z (M+H) 244.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163928B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-561dd0d8f338496d94b226926c3c9b4a
Source note	uspto-grants-2012_04