Cesium carbonate → HCID 86630931, compound

HRID 1696748Notes

Reaction equation

HRID 1696748 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([NH2:9])[N:6]=[C:5]([NH2:10])[CH:4]=1.I[CH2:12][CH2:13][F:14].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[F:14][CH2:13][CH2:12][NH:10][C:5]1[CH:4]=[C:3]([S:2][CH3:1])[CH:8]=[C:7]([NH2:9])[N:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 672745044-Methylsulfanyl-pyridine-2,6-diamine

Product 1

HCID 86630931HCID 86630931, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a glass vessel were mixed together the above prepared 4-methylsulfanyl-pyridine-2,6-diamine (0.100 g, 0.644 mmol), 1-iodo-2-fluoroethane, 0.123 g, 1.10 eq.), and 1.2 eq. of Cs2CO3 (0.252 g) in 1.0 mL of abs. acetonitrile, and the mixture allowed to react for 1 h at 125° C. in a microwave oven. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water and brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=3/7) afforded 0.037 g of the title compound as brown solid.

Workup

  1. additionIn a glass vessel were mixed together the
  2. customto react for 1 h at 125° C. in a microwave oven
  3. temperatureCooling
  4. additionpouring
  5. extractionice, twofold extraction with AcOEt
  6. washwashing with water and brine
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-562319c56b894656929ff62889a3a7fb
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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