Cesium carbonate → 5-(Cyclohexylmethyl)-4-(3,5-di-tert-butylphenyl)-1-methyl-1H-pyrrole-2-sulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-(3,5-Di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 58471046	—
Reactant	5-(Cyclohexylmethyl)-1-methyl-1H-pyrrole-2-sulfonamide	HCID 70874051	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-(Cyclohexylmethyl)-4-(3,5-di-tert-butylphenyl)-1-methyl-1H-pyrrole-2-sulfonamide	HCID 70913667	40%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A mixture of compound 25e (67.1 mg, 200 μmol), 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72.8 mg, 230 μmol), Cs2CO3 (326 mg, 1.0 mmol) and Pd(dppf)Cl2 (22 mg) in dioxane and water was heated at 110° C. under microwave irradiation for 1 h. The solvent was removed and purified by prep-TLC to afford compound 25 (35 mg, 40%) as a white solid. 1H-NMR (300 MHz, CDCl3) δ: 7.43 (t, J=1.5 Hz, 1H), 7.24 (s, 1H), 7.08 (d, J=1.5 Hz, 1H), 4.68 (s, 2H), 3.44 (s, 3H), 2.49 (d, J=7.8 Hz, 2H), 1.55-1.41 (m, 6H), 1.34 (s, 18H), 1.00-0.98 (m, 3H), 0.69-0.65 (m, 2H). MS Calcd.: 444.3; MS Found: 445.3 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946446B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-154330de5a84499db7b07c3769685a86
Source note	uspto-grants-2015_02