Cesium carbonate → N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-ylamino)ethyl)acrylamide

HRID 1774637Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH:13]=[CH2:14])[CH:5]=[CH:4][CH:3]=1.Br[C:17]1[C:18](=[O:25])[N:19]([CH3:24])[CH:20]=[C:21]([Br:23])[CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:23][C:21]1[CH:22]=[C:17]([NH:1][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH:13]=[CH2:14])[CH:5]=[CH:4][CH:3]=2)[C:18](=[O:25])[N:19]([CH3:24])[CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 105d (2.06 g, 10 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (2.65 g, 10 mmol), Pd2(dba)3 (91.6 mg, 0.1 mmol) Xant-phos (116 mg, 0.2 mmol), Cs2CO3(9.78 g, 30 mmol) in dioxane (100 mL) was degassed and stirred at 100° C. for 16 h under nitrogen. The reaction mixture was concentrated and the residue was purified by silica gel chromatography (EA/PE=5/1) to give N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-ylamino)ethyl)acrylamide 105e (2.54 g, 65%) as yellow solid. MS-ESI: [M+H]+ 394.1.

Workup

customwas degassed
concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel chromatography (EA/PE=5/1)

Sources & evidence

ORD record: ord-7ab0388c21754c0087e6bd3e8938b37e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260415B2

Reaction notes

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