Cesium fluoride → HCID 57613225, compound

HRID 910692Notes

Reaction equation

HRID 910692 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[S:36]1[CH:40]=[CH:39][CH:38]=[C:37]1[Sn](CCCC)(CCCC)CCCC.[F-].[Cs+]>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].O1CCOCC1>[CH3:14][N:11]1[CH2:12][CH2:13][N:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:37]3[S:36][CH:40]=[CH:39][CH:38]=3)[N:7]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 107272302-Chloro-6-(4-methylpiperazino)pyridine

Product 1

HCID 57613225HCID 57613225, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a vial was added 1-(6-chloro-pyridin-2-yl)-4-methyl-piperazine (27 mg, 0.13 mmol), Pd2(dba)3 (14 mg), 2-(di-t-butylphosphino)biphenyl (18 mg), 2-thienyltributylstannane (51 mg, 0.15 mmol), dioxane (1 mL) and CsF (39 mg, 0.26 mmol). The resulting mixture was heated at 100° C. for 24 hrs. The resulting mixture was extracted with EtOAc. The organic layer was dried and concentrated, and the residue was purified by preparative TLC (hexanes/EtOAc) to yield the title compound as a solid.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was purified by preparative TLC (hexanes/EtOAc)

Sources & evidence

ORD record
ord-e84f367a4c514c37bf6b86f5ba7227bb
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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