Cesium carbonate → HCID 86684342, compound

HRID 1411724Notes

Reaction equation

HRID 1411724 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.Br[C:22]1[C:23](=[O:30])[N:24]([CH3:29])[CH:25]=[C:26]([Br:28])[CH:27]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[Br:28][C:26]1[CH:27]=[C:22]([NH:1][C:2]2[N:3]=[CH:4][C:5]([N:8]3[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]3)=[N:6][CH:7]=2)[C:23](=[O:30])[N:24]([CH3:29])[CH:25]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 498399651190071-58-9

Product 1

HCID 86684342HCID 86684342, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 189d (1.1 g, 3.94 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (1.1 g, 3.94 mmol), palladium diacetate (45 mg, 0.20 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (245 mg, 0.39 mmol), and Cs2CO3 (2.6 g, 7.9 mmol) in 1,4-dioxane (150 mL) was heated at 120° C. for 2 hours. It was then cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 30:1 dichloromethane/methanol to afford 189e (900 mg, 54%). MS: [M+H]+ 465.1.

Workup

  1. temperatureIt was then cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography
  4. washeluting with 30:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-bdcc5f412e8a4f3f84391b07e3d29d49
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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