Sodium Carbonate → tert-butyl 5-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydropyridine-1(2H)-carboxylate

HRID 1530602Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:12]=1)(=O)=O.[CH3:22][N:23]1[C:27](B(O)O)=[CH:26][CH:25]=[N:24]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:22][N:23]1[C:27]([C:7]2[CH2:8][CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:12]=2)=[CH:26][CH:25]=[N:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl 5-(trifluoromethylsulfonyloxy)-3,4-dihydropyridine-1(2H)-carboxylate (2.0 g, 6.0 mmol) in dioxane (40 mL) was added 1-methyl-1H-pyrazol-5-ylboronic acid (0.83 g, 6.60 mmol), Na2CO3 (1.90 g, 18.1 mmol), and Pd(dppf)Cl2 (370 mg, 0.600 mmol). The resulting mixture was stirred at 80° C. for 18 h. After concentration, the residue was purified by silica gel chromatography eluting with a 0-25% gradient of EtOAc in petroleum ether to give tert-butyl 5-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydropyridine-1(2H)-carboxylate (0.80 g, 58% yield) as pale yellow oil. LCMS (ESI) m/z: 263.2 [M+H+].

Workup

concentrationAfter concentration
customthe residue was purified by silica gel chromatography
washeluting with a 0-25% gradient of EtOAc in petroleum ether

Sources & evidence

ORD record: ord-c29917f8864249c29b328cbe541a2598
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

Loading…