Tributylphenyltin → HCID 68461208, compound

HRID 2358802Notes

Reaction equation

HRID 2358802 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[N:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)CCC>C1(C)C=CC=CC=1.[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>[CH3:14][C:9]1[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:3]=2)[C:12]([CH3:13])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 607632TributylphenyltinHCID 59390004HCID 59390004, compound

Product 1

HCID 68461208HCID 68461208, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

2-Chloro-6-(2,5-dimethyl-pyrrol-1-yl)-pyridine (0.097 g, 0.47 mmol) prepared as described in Example 8a was reacted for 24 h with tributyl-phenyl-stannane (0.185 mL, 0.564 mmol) under nitrogen in toluene at 75° C. in the presence of 2 mole % tetrakis(triphenylphosphine) palladium(0). The volatiles were subsequently removed under reduced pressure to yield the crude product, which was purified by flash chromatography on silica gel to give the title compound (0.103 g, 88%).

Workup

  1. customThe volatiles were subsequently removed under reduced pressure
  2. customto yield the crude product, which
  3. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a711bdbcc5dd48a8886c3cd37a8c03cf
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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