2-(Tributylstannyl)pyridine → HCID 67484093, compound

HRID 2262738Notes

Reaction equation

HRID 2262738 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH2:17][N:18]4[C:26](=[O:27])[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:19]4=[O:28])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)CCC>C1COCC1.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>[N:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH2:17][N:18]4[C:19](=[O:28])[C:20]5[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:26]4=[O:27])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 67484159HCID 67484159, compound

Product 1

HCID 67484093HCID 67484093, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[1-(3-bromo-phenyl)-1H-benzimidazole-5-ylmethyl]-isoindole-1,3-dione (1.0 g, 2.31 mmol) in anhydrous THF (20 ml) was added 2-tributylstannylpyridine (0.82 ml, 2.54 mmol) and a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (60 mg) and the resultant mixture was stirred at reflux in a nitrogen atmosphere for 3 days. The reaction mixture was quenched with aqueous ammonia and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate and concentrated in vacuo. The concentrate was eluted through silica gel with ethyl acetate to afford the desired product. 0.24 g (24%).

Workup

  1. temperatureat reflux in a nitrogen atmosphere for 3 days
  2. customThe reaction mixture was quenched with aqueous ammonia
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. washThe concentrate was eluted through silica gel with ethyl acetate

Sources & evidence

ORD record
ord-65c9af31f1c6419396d0adbc0a54011b
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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