2-(Tri-n-butylstannyl)thiophene → 1-Methyl-4-(5-thiophen-2-yl-pyridin-3-yl)-piperazine

HRID 910693

Reaction equation

HRID 910693 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[Sn](CCCC)(CCCC)CCCC>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.O1CCOCC1>[CH3:14][N:11]1[CH2:12][CH2:13][N:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([C:16]3[S:15][CH:19]=[CH:18][CH:17]=3)[CH:3]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 534853141-(5-Bromopyridin-3-yl)-4-methylpiperazine

Product 1

HCID 226322881-Methyl-4-(5-thiophen-2-yl-pyridin-3-yl)-piperazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a vial was added 1-(5-bromo-pyridin-3-yl)-4-methyl-piperazine (47 mg, 0.13 mmol), Pd(PPh3)4 (34 mg), 2-thienyltributylstannane (67 mg, 0.15 mmol) and dioxane (1 mL). 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-f590971f92df40c184810059889b07ef
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Linked notes

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