Potassium Carbonate → tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 2087255Notes

Reaction equation

CC(C)(C)C(O[N:6]1[CH2:11][CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[CH2:8][CH2:7]1)=O.[C:23]([O-:26])([O-])=[O:24].[K+].[K+].Br[C:30]1[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[CH:33]=[CH:34][C:35]=1[CH3:36]>CN(C=O)C>[C:38]([NH:37][C:32]1[CH:31]=[CH:30][C:35]([CH3:36])=[C:34]([C:9]2[CH2:8][CH2:7][N:6]([C:23]([O:26][C:35]([CH3:36])([CH3:34])[CH3:30])=[O:24])[CH2:11][CH:10]=2)[CH:33]=1)(=[O:42])[CH:39]([CH3:41])[CH3:40]

Participants

Conditions

Temperature: 80 °C

Procedure

To a 50-mL RB flask containing 1-[(2,2-dimethylpropanoyl)oxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (500 mg, 1.62 mmol), K2CO3 (670 mg, 4.86 mmol) and PdCl2dppf (155 mg) was added a solution of N-(3-bromo-4-methylphenyl)-2-methylpropanamide (415 mg, 1.62 mmol) in DMF (10.0 mL) at room temperature under argon. The mixture was heated to 80° C. under argon overnight. After cooled to room temperature, the mixture was filtered through celite and the celite was washed with EtOAc (3×20 mL). The filtrates were washed with H2O (20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified flash chromatography (20% EtOAc/hexane) to give tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate (360 mg, 62.0%)

Workup

temperatureAfter cooled to room temperature
filtrationthe mixture was filtered through celite
washthe celite was washed with EtOAc (3×20 mL)
washThe filtrates were washed with H2O (20 mL), brine (20 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified flash chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record: ord-5fff664841814d7e89e1195f96cd606f
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727264B1

Reaction notes

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