Chloroform → HCID 11688663, compound

HRID 2219468Notes

Reaction equation

HRID 2219468 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[C:16](I)=[CH:15][CH:14]=[C:13]([CH3:18])[N:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=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.C(Cl)(Cl)Cl>O1CCOCC1.C(Cl)Cl.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:8][C:9]([C:11]2[C:16]([NH:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:15][CH:14]=[C:13]([CH3:18])[N:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 6212ChloroformHCID 100093-AminopyridineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86607565HCID 86607565, compound

Product 1

HCID 11688663HCID 11688663, compoundYield 24.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

In a 5 ml microwave reaction vessel were dissolved 50 mg (0.134 mmol) 3-Iodo-6-methyl-pyridine-2-carboxylic acid (3-chloro-phenyl)-amide and 16 mg (0.168 mmol, 1.25 equiv.) of 3-aminopyridine in 2 ml of dioxane. Cesium carbonate (61 mg, 188 mmol, 1.4 equiv.) were added and argon was bubbled through the suspension for 3 min. Then Xanthphos (26 mg, 0.044 mmol, 0.33 equiv.) and Pd2(dba)3.CHCl3 14 mg (0.013 mmol, 0.1 equiv.) were added and the mixture was heated for 30 min at 150° C. under microwave irradiation. The mixture was diluted with methylene chloride, filtered and concentrated in vaccuo. The resulting dark brown oil (129 mg) was purified by flash chromatography (gradient: heptane/ethyl acetate 4:1 to 3:2) to yield the title compound as a yellow solid (total 11 mg, 24%), MS (ISP): m/e=339.1, 341.1 (M+H+).

Workup

  1. customargon was bubbled through the suspension for 3 min
  2. filtrationfiltered
  3. concentrationconcentrated in vaccuo
  4. customThe resulting dark brown oil (129 mg) was purified by flash chromatography (gradient: heptane/ethyl acetate 4:1 to 3:2)

Sources & evidence

ORD record
ord-2a59da38e76a4e3ebb93dd1563c3f82d
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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