Chloroform → HCID 11688679, compound

HRID 2219472Notes

Reaction equation

HRID 2219472 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([CH3:18])[N:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.Br[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.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:7]=[C:6]([NH:8][C:9]([C:11]2[C:16]([NH:17][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:4][N:3]=1

Participants

8

Reactant 5

HCID 6212ChloroformHCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86607567HCID 86607567, compound

Product 1

HCID 11688679HCID 11688679, compoundYield 41%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
160 °C

Procedure

In a 5 ml microwave reaction vessel were dissolved 80 mg (0.31 mmol) 3-Amino-6-methyl-pyridine-2-carboxylic acid (2-chloro-pyridin-4-yl)-amide and 60 mg (0.38 mmol, 1.25 equiv.) of 3-Bromopyridine in 4 ml of dioxane. Cesium carbonate (139 mg, 0.43 mmol, 1.4 equiv.) were added and argon was bubbled through the suspension for 3 min. Then Xanthphos (58 mg, 0.10 mmol, 0.33 equiv.) and Pd2(dba)3.CHCl3 (32 mg, 0.03 mmol, 0.1 equiv.) were added and the mixture was heated for 2 h at 160° C. under microwave irradiation. To the mixture was added silica gel (5 g) and the mixture was evaporated to dryness in vaccuo. The powder was charged onto a flash chromatography column and eluted (heptane/ethyl acetate 2:1) to yield the title compound as a yellow solid (total 43 mg, 41%), MS (ISP): m/e=340.1, 342.0 (M+H+).

Workup

  1. customargon was bubbled through the suspension for 3 min
  2. additionTo the mixture was added silica gel (5 g)
  3. customthe mixture was evaporated to dryness in vaccuo
  4. additionThe powder was charged onto a flash chromatography column
  5. washeluted (heptane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-7672228fa90744a78b45afa69ab3fd08
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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