Cesium carbonate → HCID 11616994, compound

HRID 2219475Notes

Reaction equation

HRID 2219475 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.[F:25]C1C=NC=C(F)C=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[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]=[C:22]([F:25])[CH:23]=3)=[CH:15][CH:14]=[C:13]([CH3:24])[N:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6428203,5-DifluoropyridineHCID 11522606HCID 11522606, compound

Product 1

HCID 11616994HCID 11616994, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a 5 ml microwave reaction vessel were dissolved 70 mg (0.29 mmol) 3-Amino-6-methyl-pyridine-2-carboxylic acid (2-methyl-pyridin-4-yl)-amide (Example 5) and 266 mg (2.31 mmol, 8.0 equiv.) of 3,5-difluoropyridine in 1.5 ml of DMF. Cesium carbonate (376 mg, 1.16 mmol, 4.0 equiv.) was added and the suspension was sonicated under argon for 10 min. The mixture was heated for 72 h at 120° C. in an oil bath and then 1 h at 160° C. under microwave irradiation. The dark brown suspension was filtered over Dicalite which was washed with ethyl acetate. The filtrate was evaporated to dryness in vaccuo, and the residue dissolved in 200 ml of ethyl acetate, which was washed once with brine. After drying over magnesium sulfate and concentration in vaccuo, the residue (90 mg) was purified by flash chromatography (gradient heptane/ethyl acetate 1:1 to 0:1 ) to yield the title compound, light yellow solid, (23 mg, 24%). MS (ISP): m/e=338.1 (M+H+).

Workup

  1. customthe suspension was sonicated under argon for 10 min
  2. custom1 h at 160° C. under microwave irradiation
  3. filtrationThe dark brown suspension was filtered over Dicalite which
  4. washwas washed with ethyl acetate
  5. customThe filtrate was evaporated to dryness in vaccuo
  6. dissolutionthe residue dissolved in 200 ml of ethyl acetate
  7. washwhich was washed once with brine
  8. dry with materialAfter drying over magnesium sulfate and concentration in vaccuo
  9. customthe residue (90 mg) was purified by flash chromatography (gradient heptane/ethyl acetate 1:1 to 0:1 )

Sources & evidence

ORD record
ord-82b79f5754c34d74805a75f75d73406f
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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