2-(Tributylstannyl)pyridine → HCID 70201544, compound

HRID 342456Notes

Reaction equation

HRID 342456 reaction equation
Br[C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:4]=2[O:5][C:6]=1[CH3:7].C([Sn](CCCC)(CCCC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)CCC>COCCOC.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>[ClH:20].[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:13]([NH:12][C:8]1[C:4]2[O:5][C:6]([CH3:7])=[C:2]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[C:3]=2[CH:11]=[CH:10][CH:9]=1)=[O:22]

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 70199045HCID 70199045, compound

Product 1

HCID 70201544HCID 70201544, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-bromo-7-(2,6-dichlorobenzoylamino)-2-methylbenzo[b]furan (165 mg), 2-(tributylstannyl)pyridine (213 mg) and tetrakis(triphenylphosphine)palladium (10 mg) in 1,2-dimethoxyethane (3 ml) was refluxed for 18 hours. The reaction mixture was evaporated in vacuo and the residue was purified by column chromatography on silica gel. The obtained oil was dissolved in methanolic hydrogen chloride and to the solution was evaporated in vacuo. The residue was crystallized from ethyl acetate to give 7-(2,6-dichlorobenzoylamino)-2-methyl-3-(pyridin-2-yl)benzo[b]furan hydrochloride (45 mg).

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe residue was purified by column chromatography on silica gel
  4. dissolutionThe obtained oil was dissolved in methanolic hydrogen chloride and to the solution
  5. customwas evaporated in vacuo
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-84a6f39d2a8b40c4ad965f3851045f05
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

Loading…