Sodium Carbonate → 2-Tert-butoxycarbonylamino-5-(2-tert-butylaminosulfonyl-phenyl)-phenyl carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-	HCID 4997616	—
Reactant	1,2-Di(tert-Butyloxycarbonylamino)-4-bromobenzene	HCID 13007803	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	2-Tert-butoxycarbonylamino-5-(2-tert-butylaminosulfonyl-phenyl)-phenyl carbamic acid tert-butyl ester	HCID 57935033	100.9%

Reaction Steps

A solution of (5-bromo-2-tert-butoxycarbonylamino-phenyl)-carbamic acid tert-butyl ester (4.0 g, 10.3 mmol), 2-(tert-butylaminosulfonyl)-phenyl boronic acid (5.3 g; 20.6 mmol), PdCl2 dppf (1.7 g, 0.20 mmol) and 1M Na2CO3 solution (83 mL, 82.7 mmol) in 1,2-dimethoxyethane was heated to 90° C. for 12 h under inert atmosphere. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by chromatography (silica, EtOAc: hexanes, 3:7) to afford the title compound as a yellow viscous oil (5.4 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.14 (m, 1H), 7.88 (m, 1H), 7.43-7.69 (m, 6H), 7.19 (m, 1H), 7.28 (m, 1H), 1.52 (s, 9H), 1.48 (s, 9H), 1.06 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C26H37N3O6S: 520.65 (M+H), Found 520.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612211B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-6f821a3a4b0e40c78dc39b986c1f4f43
Source note	uspto-grants-2009_11