Chloroform → HCID 86607573, compound

HRID 2219488Notes

Reaction equation

HRID 2219488 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:14]=[C:13]([CH3:24])[N:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.Br[C:26]1C=NC=CC=1C.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]>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[CH3:26])=[CH:15][CH:14]=[C:13]([CH3:24])[N:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 6212ChloroformHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 8176303-Bromo-4-methylpyridineHCID 11522606HCID 11522606, compound

Product 1

HCID 86607573HCID 86607573, compoundYield 36.5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
130 °C

Procedure

In a 10 ml reaction vessel were dissolved 55 mg (0.23 mmol) 3-Amino-6-methyl-pyridine-2-carboxylic acid (2-chloro-pyridin-4-yl)-amide (example 5) and 81 mg (0.45 mmol, 2.0 equiv.) of 3-Bromo-4-methylpyridine in 3 ml of dioxane. Cesium carbonate (148 mg, 0.45 mmol, 2.0 equiv.) were added and argon was bubbled through the suspension for 3 min. Then Xanthphos (43 mg, 0.075 mmol, 0.33 equiv.) and Pd2(dba)3.CHCl3 (23.5 mg, 0.023 mmol, 0.1 equiv.) were added, the vessel was closed and the mixture was heated for 19 h at 130° C. To the mixture was added silicagel (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 4:1) to yield the title compound as a yellow crystalline solid (total 28 mg, 28%), MS (ISP): m/e=334.0 (M+H+).

Workup

  1. customIn a 10 ml reaction vessel
  2. customargon was bubbled through the suspension for 3 min
  3. customthe vessel was closed
  4. additionTo the mixture was added silicagel (5 g)
  5. customthe mixture was evaporated to dryness in vaccuo
  6. additionThe powder was charged onto a flash chromatography column
  7. washeluted (heptane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-c6934d5c93b84b07a1cd350ac5f931f4
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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