Sodium Carbonate → tert-butyl 4-(3-methoxy-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1804705Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)O1.Cl[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[C:26]([O:33][CH3:34])[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:34][O:33][C:26]1[CH:25]=[C:24]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH:10]=2)[CH:29]=[CH:28][C:27]=1[N+:30]([O-:32])=[O:31]

Participants

Conditions

Temperature: 130 °C

Procedure

Into a 5 mL microwave tube was charged tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.247 g, 0.800 mmol), 4-chloro-2-methoxy-1-nitrobenzene (0.100 g, 0.533 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.019 g, 0.027 mmol), sodium carbonate (0.113 g, 1.066 mmol) in water (0.889 ml) and dimethoxyethane (2.3 ml). The reaction mixture was heated at 130° C. for 20 minutes in a Biotage microwave reactor. The solids were filtered off and the filtrate was purified by reverse phase HPLC using 0.1% ammonium hydroxide. MS (DCI(+)) m/e 335.2 (M+H)+.

Workup

filtrationThe solids were filtered off
customthe filtrate was purified by reverse phase

Sources & evidence

ORD record: ord-09e2fb25257d485ca29f7b0e742a41b1
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354422B2

Reaction notes

Loading…