Dimethylformamide → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Ethyl Acetate	HCID 8857	—
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-methoxy-1,3-benzothiazole	HCID 11218765	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine	HCID 24803565	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 2-bromo-6-methoxy-benzothiazole (1.14 g), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.23 g, 1.2 eq.), Pd(dppf)Cl2*DCM (170 mg, 0.05 eq.) and 2.0 M aq. K2CO3 (10 ml, 4 eq.) in DMF (20 ml) was heated at 80° C. for 2 h under argon while stirring. Ethyl acetate (200 ml) was subsequently added before concentrating the sol. onto diatomaceous earth in vacuo. Purification by flash chromatography (DCM:methanol, 99:1 to 95:5) provided the title compound (730 mg) as a yellow solid. 1H NMR δ 8.56 (d, 1H) 7.96 (dd, 1H) 7.82 (d, 1H) 7.64 (d, 1H) 7.07 (dd, 1H) 6.67 (br. s, 2H) 6.55 (d, 1H) 3.83 (s, 3H); MS m/z (M+H) 258.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163928B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-7f6868da1f284daca2a8f5e0c5402880
Source note	uspto-grants-2012_04