Water → 4-(4-Ethoxycarbonyl-thiophen-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Ethyl 5-bromothiophene-3-carboxylate	HCID 15293216	—
Reactant	tert-butyl 4-(3,3,4,4-tetramethylborolan-1-yl)-5,6-dihydropyridine-1(2H)-carboxylate	HCID 68758613	—
Catalyst	HCID 178420534	HCID 178420534	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	4-(4-Ethoxycarbonyl-thiophen-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester	HCID 59542587	56.3%

Reaction Conditions

Temperature	120 °C

Reaction Steps

2-Bromothiophene-4-carboxylic acid ethyl ester (1.0 g, 5.26 mmol) and 4-(3,3,4,4-tetramethyl-borolan-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (5.26 mmol) were dissolved in DME (40 mL), IMS (20 mL) and water (10 mL). Palladium tetrakis-triphenylphoshine (0.53 mmol) and caesium carbonate (7.9 mmol) were then added and the mixture heated to 120° C. for 20 minutes using microwave radiation. The solvent was then evaporated and the residue purified by flash chromatography on silica, eluting with 0-40% ethyl acetate in cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a clear oil (1.0 g). LCMS m/z 238.06 [M+H]+ RT=4.33min (Analytical Method 4).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08362008B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-7882d512d5f64a5287386568f78cc60e
Source note	uspto-grants-2013_01