4-(Tri-n-butylstannyl)pyridine → HCID 67747269, compound

HRID 1901108Notes

Reaction equation

HRID 1901108 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)CCC.[CH2:20]([O:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[C:30](Br)[CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([C:6]2[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=2)[CH:31]=[C:32]([F:34])[CH:33]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzene

Product 1

HCID 67747269HCID 67747269, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-tributylstannylpyridine (250 mg), O-benzyl-3-bromo-5-fluorophenol (200 mg; EP 385,662) and tetrakis (triphenylphosphine) palladium (8 mg) in dioxane (3 mL) was heated at 100° C. for 15 h. The solvent was evaporated and the residue chromatographed (silica gel; hexane/EtOAc acetate (4:1-3:2)) to provide the title compound as an oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue chromatographed (silica gel; hexane/EtOAc acetate (4:1-3:2))

Sources & evidence

ORD record
ord-58a19089502b48ba83f233e6ee65d590
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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