Cesium carbonate → HCID 86684120, compound

HRID 1024012Notes

Reaction equation

HRID 1024012 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][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)=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24](Br)[C:25]2[N:26]([CH:28]=[CH:29][N:30]=2)[CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>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].O1CCOCC1>[Cl:21][C:22]1[CH:23]=[C:24]([NH:1][C:2]2[N:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[C:25]2[N:26]([CH:28]=[CH:29][N:30]=2)[CH:27]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylateHCID 263700388-Bromo-6-chloroimidazo(1,2-a)pyridine

Product 1

HCID 86684120HCID 86684120, compoundYield 78%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (60 mL), tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (1.5 g, 5.39 mmol), 8-bromo-6-chloroimidazo[1,2-a]pyridine 101a (3.7 g, 16.18 mmol), and cesium carbonate (3.52 g, 10.79 mmol). XantPhos (312 mg, 0.539 mmol) and Pd2(dba)3 (494 mg, 0.539 mmol) were added, and the reaction mixture was heated at 100° C. for 5 h under nitrogen. After this time the reaction was cooled to room temperature. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified on flash column eluting with 100:1 CH2Cl2/MeOH to afford 102a (1.8 g, 78%). MS: [M+H]+ 429.

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureAfter this time the reaction was cooled to room temperature
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified on flash column
  7. washeluting with 100:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-17376b86b8bc4f828a72a5b39ac79078
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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