Cesium fluoride → HCID 90118285, compound

HRID 523143

Reaction equation

HRID 523143 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:24]1[CH:29]=[N:28][CH:27]=[CH:26][N:25]=1)CCC.[F-].[Cs+]>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=[C:2]([C:24]2[CH:29]=[N:28][CH:27]=[CH:26][N:25]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27373162-(Tributylstannyl)pyrazineHCID 901180792,4-Dichloro-6-(4-isopropoxyphenyl)pyridine

Product 1

HCID 90118285HCID 90118285, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a 2 dram vial equipped with a stir bar was added 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine (50 mg, 0.18 mmol), 2-(tributylstannyl)pyrazine (65 mg, 0.18 mmol), CuI (9.0 mg, 0.047 mmol), CsF (82 mg, 0.54 mmol), and Pd(PPh3)4 (10.2 mg, 8.86 μmol). The vial was capped with a septum screw-cap and then placed under N2 atmosphere. To the vial was added degassed DMF (1 mL). The vial was placed in a 80° C. heating block with stirring for 1 hour. The reaction mixture was directly purified by C18 chromatography (water:MeOH w/0.1% TFA) to afford 2-(4-chloro-6-(4-isopropoxyphenyl)pyridin-2-yl)pyrazine as a dark solid (37 mg, 64%).

Workup

  1. customTo a 2 dram vial equipped with a stir bar
  2. customThe vial was capped with a septum
  3. customscrew-cap
  4. additionTo the vial was added
  5. customdegassed DMF (1 mL)
  6. customwas placed in a 80° C.
  7. temperatureheating block
  8. customThe reaction mixture was directly purified by C18 chromatography (water:MeOH w/0.1% TFA)

Sources & evidence

ORD record
ord-71c5379fc1e0476e842fe6f6a6054db7
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Linked notes

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