tert-Butyl carbamate → HCID 58337569, compound

Participants

Role	Name	HCID	Charge
Reactant	tert-Butyl carbamate	HCID 77922	—
Reactant	Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane	HCID 11618717	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	HCID 58337657	HCID 58337657	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Toluene	HCID 1140	—
Product	HCID 58337569	HCID 58337569	75%

Reaction Steps

Compound 7 (50 mg, 0.17 mmol, 1.0 eq), tert-butyl carbamate (25 mg, 0.21 mmol, 1.2 eq), sodium tert-butoxide (24 mg, 0.25 mmol, 1.4 eq), Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (5.4 mg, 0.0052 mmol, 0.030 eq), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (8 mg, 0.02 mmol, 0.09 eq) and toluene (0.65 mL) were added to a round-bottom flask, purged with argon and stirred at room temperature overnight. The reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 41 mg (73%) of the title compound as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 9.05 (s, 1H), 8.55 (s, 2H), 7.26 (s, 1H), 7.18 (s, 1H), 6.90 (s, 1H), 6.73 (t, J=1.9 Hz, 1H), 1.54 (s, 9H); ES-MS [M+1]+: 322.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08501757B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-095a8b8ccf4148189646c3b63326fffd
Source note	uspto-grants-2013_08