Cesium carbonate → HCID 86684119, compound

HRID 1024001Notes

Reaction equation

HRID 1024001 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](Br)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=2)[CH2:15][CH2:14]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+]>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]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([N:16]3[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]3)=[CH:24][N:23]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 223298335-(4-Methylpiperazin-1-yl)pyridin-2-amineHCID 263700388-Bromo-6-chloroimidazo(1,2-a)pyridine

Product 1

HCID 86684119HCID 86684119, compoundYield 44%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A mixture of 101a (2.3 g, 10 mmol), 5-(4-methylpiperazin-1-yl)pyridin-2-amine (1.9 g, 10 mmol), XantPhos (576 mg, 1.0 mmol), Pd2(dba)3 (915 mg, 1.0 mmol) and Cs2CO3 (6.5 g, 20 mmol) in dioxane (50 mL) was heated at 100° C. for 12 h under nitrogen. It was then filtered and evaporated in vacuo. The residue was purified by silica-gel column eluting with 1:1 ethyl acetate/petroleum ether to afford 101b as a green solid (1.5 g, 44%). MS: (M+H)+ 343.

Workup

  1. filtrationIt was then filtered
  2. customevaporated in vacuo
  3. customThe residue was purified by silica-gel column
  4. washeluting with 1:1 ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-f53bc8b6ef59464ea3ee84ac590c234d
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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