Cesium carbonate → HCID 118116911, compound

HRID 1774663Notes

Reaction equation

HRID 1774663 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])[CH2:9]2)[CH:5]=[CH:4][CH:3]=1.Br[C:20]1[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=[C:24]([Br:26])[CH:25]=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:26][C:24]1[CH:25]=[C:20]([NH:1][C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])[CH2:9]3)[CH:5]=[CH:4][CH:3]=2)[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=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 118116346HCID 118116346, compound

Product 1

HCID 118116911HCID 118116911, compoundYield 28.4%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
95 °C

Procedure

A mixture of 114e (440 mg, 1.79 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 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 (S)—N-(1-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yl)piperidin-3-yl)acrylamide 114f (220 mg, 28%) as yellow solid. MS-ESI: [M+H]+ 433.3

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-1b0a947a22d84cf5abd6dab43a9a1b86
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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