Cesium carbonate → HCID 118116564, compound

HRID 1774652Notes

Reaction equation

HRID 1774652 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:16])[CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH:13]=[CH2:14])[CH:5]=[CH:4][CH:3]=1.Br[C:18]1[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=[C:22]([Br:24])[CH:23]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC(=O)OCC.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:24][C:22]1[CH:23]=[C:18]([NH:1][C:2]2[N:7]=[C:6]([N:8]([CH3:16])[CH2:9][CH2:10][NH:11][C:12](=[O:15])[CH:13]=[CH2:14])[CH:5]=[CH:4][CH:3]=2)[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 118117179HCID 118117179, compound

Product 1

HCID 118116564HCID 118116564, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 110e (400 mg, 1.82 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (534 mg, 2.0 mmol), Pd2(dba)3 (83 mg, 0.091 mmol), Xantphos (105 mg, 0.182 mmol) and Cs2CO3 (1.48 g, 4.55 mmol) in DMF (10 mL) was stirred at 95° C. under N2 for 7 h. The mixture was diluted with EA (50 mL) and filtered. The filtrate was washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (PE/EA=1/2) to give N-(2-((6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yl)(methyl)amino)ethyl)acrylamide 110f (160 mg, 22%) as a yellow solid. ESI-LCMS: m/z=408.0

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (PE/EA=1/2)

Sources & evidence

ORD record
ord-261f311a36db49bebdca2b4a41b1ff17
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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