Sodium Carbonate → tert-butyl 4-(4-amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylate

HRID 1503890Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([O:9][CH3:10])[CH:3]=1.CC1(C)C(C)(C)CB([C:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=2)C1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=2)=[CH:3][C:4]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-bromo-2-methoxybenzenamine (1.21 g, 6.0 mmol), tert-butyl 4-(3,3,4,4-tetramethylborolan-1-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.95 g, 6.3 mmol), sodium carbonate (1.91 g, 18 mmol) and 1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.22 g, 0.3 mmol) in dioxane (25 mL) and water (5 mL) was degassed with nitrogen and heated to 90° C. for 15 hours. After cooling to ambient temperature, the mixture was filtered, concentrated and purified by flash chromatography eluting with 200:1 dichloromethane:methanol to give the title compound. MS: 305 (M+H+).

Workup

customwas degassed with nitrogen
temperatureAfter cooling to ambient temperature
filtrationthe mixture was filtered
concentrationconcentrated
custompurified by flash chromatography
washeluting with 200:1 dichloromethane

Sources & evidence

ORD record: ord-c021e38bd1444f8985eb3d240a724852
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212192B2

Reaction notes

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