Potassium Phosphate, Tribasic → tert-Butyl 4-(7-bromo-2-naphthyl)-3-oxopiperazine-1-carboxylate

HRID 1465745Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Br:12])=[CH:7][CH:8]=2)[CH:3]=1.[O:13]=[C:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.CNC1CCCCC1NC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.O1CCOCC1>[Br:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([N:19]3[CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:15][C:14]3=[O:13])=[CH:3]2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a 20 mL microwave vial charged with 2,7-dibromonaphthalene (1.1 g, 3.8 mmol), tert-butyl 3-oxopiperazine-1-carboxylate (0.50 g, 2.5 mmol), and a stir bar was added copper (I) iodide (95 mg, 0.50 mmol), N,N′-dimethylcyclohexane-1,2-diamine (142 mg, 1.0 mmol), K3PO4 (1100 mg, 5.0 mmol), and dioxane (15 mL). The mixture was purged three times with nitrogen, and heated to 150° C. in a microwave reactor. The crude solution was diluted with EtOAc, adsorbed onto silica gel, and purified by silica gel chromatography (Hex:EtOAc). The solvent was removed to provide the title compound. LC-MS (IE, m/z): 405 [M+1]+.

Workup

customThe mixture was purged three times with nitrogen
additionThe crude solution was diluted with EtOAc
custompurified by silica gel chromatography (Hex:EtOAc)
customThe solvent was removed

Sources & evidence

ORD record: ord-c0d3925e28e445d2a7e268e18f092f10
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999991B2

Reaction notes

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