Cesium carbonate → HCID 58043709, compound

HRID 1918996Notes

Reaction equation

HRID 1918996 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:11][C:10]([CH3:13])([OH:12])[CH2:9]2)=[CH:4][CH:3]=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.Br[C:57]1[C:58](=[O:65])[N:59]([CH3:64])[CH:60]=[C:61]([Br:63])[CH:62]=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:63][C:61]1[CH:62]=[C:57]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:11][C:10]([OH:12])([CH3:13])[CH2:9]3)=[CH:6][N:7]=2)[C:58](=[O:65])[N:59]([CH3:64])[CH:60]=1

Participants

7

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 58044268HCID 58044268, compound

Product 1

HCID 58043709HCID 58043709, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 207b (1.84 g, 10.3 mmol), XantPhos (714 mg, 1.24 mmol), Pd2 dba3 (755 mg, 0.82 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (3.27 g, 12.3 mmol) and Cs2CO3 (10 g. 30.9 mmol) in 1,4-dioxane (50 mL) was heated at reflux for 2 h. After the completion of the reaction, the mixture was filtered off, and washed with MeOH (100 mL). The filtrate was evaporated in vacuo and the residue was purified on reverse phase Combi-flash to give 207c (2.11 g, 54%). MS: [M+H]+ 365.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customAfter the completion of the reaction
  4. filtrationthe mixture was filtered off
  5. washwashed with MeOH (100 mL)
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified on reverse phase Combi-flash

Sources & evidence

ORD record
ord-2af6e38c5ee34ddaa5328618029d86a3
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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