5-Bromo-N-methylpyridin-2-amine → 5-[1,3]Dioxolo[4,5-f][1,3]benzothiazol-6-yl-N-methylpyridin-2-amine

Participants

Role	Name	HCID	Charge
Reactant	5-Bromo-N-methylpyridin-2-amine	HCID 15645663	—
Reactant	[1,3]Dioxolo[4',5':4,5]benzo[1,2-d]thiazole	HCID 20557021	—
Reactant	2-(2-Methoxypyrimidin-5-yl)-1,3-benzothiazole	HCID 24803726	—
Catalyst	Bis(tri-tert-butylphosphine)palladium(0)	HCID 2734558	—
Product	5-[1,3]Dioxolo[4,5-f][1,3]benzothiazol-6-yl-N-methylpyridin-2-amine	HCID 24804399	35.7%

Reaction Conditions

Temperature	170 °C

Reaction Steps

To [1,3]Dioxolo[4,5-f][1,3]benzothiazole (98 mg, 0.55 mmol) and 5-bromo-N-methylpyridin-2-amine (112 mg, 0.60 mmol) were subjected to the procedure used for the preparation of 2-(2-methoxypyrimidin-5-yl)-1,3-benzothiazole, with the following exceptions: 5 mol % bis(tri-t-butylphosphine) palladium (0) was used and the reaction was heated under argon at 170° C. in a microwave oven for 30 min. The crude material was purified by flash chromatography (Heptane/EtOAc 1:1) to give the title compound (56 mg) as a yellow solid. 1H NMR δ 8.62 (d, 1H) 7.94 (dd, 1H) 7.61 (s, 1H) 7.47 (s, 1H) 7.19 (q, 1H) 6.57 (d, 1H) 6.13 (s, 2H) 2.85 (d, 3H); MS m/z (M+H) 286.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163928B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-568de3695f204747b080debcad9088a0
Source note	uspto-grants-2012_04