Potassium Carbonate → 2-(1-(6-methyl-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-2-yl)-ethyl)isoindoline-1,3-dione

HRID 405990Notes

Reaction equation

[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[C:16](=[O:17])[N:15]2[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:14]2=[N:13][C:12]=1[CH:23]([N:25]1[C:33](=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]1=[O:35])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>O.O1CCOCC1.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:22][C:18]1[N:15]2[C:16](=[O:17])[C:11]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:12]([CH:23]([N:25]3[C:33](=[O:34])[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26]3=[O:35])[CH3:24])[N:13]=[C:14]2[CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of phenylboronic acid (0.177 g, 1.45 mmol), 2-(1-(3-bromo-6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)isoindoline-1,3-dione (Prepared in Example 6, 0.40 g, 0.97 mmol) and potassium carbonate (0.402 g, 2.91 mmol) in a mixture of water (0.5 mL) and dioxane (9 mL) was added dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (0.040 g, 0.049 mmol) under an argon atmosphere. The mixture was stirred at 90° C. for 3 h then was loaded onto silica gel and purified by MPLC (eluted with a gradient of 0-3% MeOH in DCM) to afford 2-(1-(6-methyl-4-oxo-3-phenyl-4H-pyrido[1,2-a]-pyrimidin-2-yl)ethyl)isoindoline-1,3-dione as a yellow solid. Mass Spectrum (ESI) m/e=410.1 (M+1).

Workup

custompurified by MPLC (
washeluted with a gradient of 0-3% MeOH in DCM)

Sources & evidence

ORD record: ord-27835a690963410ab4859fc17703a6d6
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754089B2

Reaction notes

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