Ethyl Acetate → US10023592, Example 315

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one	HCID 45480194	—
Reactant	1-(2-Cyclopropylethyl)-2-iodo-4-methylsulfonylbenzene	HCID 118021966	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	N,N-Dimethylformamide--water (1/1)	HCID 21962138	—
Product	US10023592, Example 315	HCID 118021519	55%

Reaction Steps

The title compound of step 3 (120 mg, 0.34 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (89 mg, 0.37 mmol), Na2CO3 (72 mg, 0.68 mmol) and Pd(dppf)Cl2 (15 mg) in DMF/H2O (6 ml/1.5 ml) under N2 were heated at100° C. for 1 h. EA extractive work up and preparative TLC (PE:EtOAc=0:1) gave the title compound (62 mg, 55%). 1H NMR (CD3OD, 400 MHz): δ 7.92 (dd, J1=2.4 Hz, J2=5.6 Hz, 1H), 7.81 (d, J=2 Hz, 1H), 7.78 (d, J=2.4 Hz, 1H), 7.65-7.61 (m, 2H), 6.69 (m, J=9.2 Hz, 1H), 3.69 (s, 3H), 3.17 (s, 3H), 2.89-2.86 (m, 2H), 1.51-1.45 (m, 2H), 0.68-0.65 (m, 1H), 0.45-0.40 (m, 2H), 0.04-0.00 (m, 2H). LCMS: 332 (M+1)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034900B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-323d4768c9154bcea656dafaa0b075e5
Source note	uspto-grants-2015_05