Water → Methyl 2-amino-3-(4-(diisopropylcarbamoyl)pyridin-3-yl)benzoate

https://huagongshe.com/reaction/1919681

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Methyl 2-amino-3-bromobenzoate	HCID 11615550	—
Reactant	{4-[Di(propan-2-yl)carbamoyl]pyridin-3-yl}boronic acid	HCID 57500682	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 2-amino-3-(4-(diisopropylcarbamoyl)pyridin-3-yl)benzoate	HCID 50941398	31%

Reaction Steps

Methyl 2-amino-3-bromobenzoate (1.0 eq, 652 mg, 2.61 mmol) and 4-(diisopropylcarbamoyl)pyridin-3-ylboronic acid (prepared according to the procedure described in PCT patent application WO2005/105814, 1.0 eq, 600 mg, 2.61 mmol) were combined with cesium carbonate (2.0 eq, 1.699 g, 5.21 mmol) in dioxane containing 5% of water (6 ml). The mixture was degassed by bubbling nitrogen for 10 minutes. PdCl2(dppf) (0.05 eq, 95 mg) was added and the reaction stirred at reflux for 2 hours. Dioxane was evaporated, water was added and the material extracted with CH2Cl2 (3×). The combined extracts were dried over Na2SO4 and the solvents removed in vacuo. The material was purified by flash chromatography on silica gel (eluant 0.5% MeOH in CH2Cl2) to afford methyl 2-amino-3-(4-(diisopropylcarbamoyl)pyridin-3-yl)benzoate as a greenish foam (244 mg, 31% yield). LCMS (ES): >95% pure, m/z 356 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08168651B2
Source dataset	uspto-grants-2012_05
ORD ID	ord-8cba6f96394b46fc9ca5c5eb9472a1b9
Source note	uspto-grants-2012_05