5-Bromo-1-benzofuran-7-carbaldehyde → HCID 15428564, compound

HRID 1584773Notes

Reaction equation

HRID 1584773 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH3:13][N:14]1[C:18]([Sn](CCCC)(CCCC)CCCC)=[CH:17][N:16]=[N:15]1>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:13][N:14]1[C:18]([C:2]2[CH:3]=[C:4]([CH:11]=[O:12])[C:5]3[O:9][CH:8]=[CH:7][C:6]=3[CH:10]=2)=[CH:17][N:16]=[N:15]1

Participants

6

Reactant 2

HCID 212208405-Bromo-1-benzofuran-7-carbaldehydeHCID 226098261-methyl-5-(tributylstannyl)-1H-1,2,3-triazole

Product 1

HCID 15428564HCID 15428564, compoundYield 251.5%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 5-bromo-benzofuran-7-carbaldehyde (0.315 g), 1-methyl-5-tributylstannanyl-1H-[1,2,3]-triazole (0.525 g) and bis(triphenylphosphine)palladium (II) chloride (0.05 g) in toluene (7 ml) was stirred and refluxed under nitrogen for 5 h. The cooled mixture was diluted with 8% sodium bicarbonate (30 ml) and extracted with ethyl acetate (3×25 ml). The combined extracts were dried (MgSO4) and the solvent removed in vacuo to give a yellow solid (0.8 g). Purification by FCC, eluting with ethyl acetate-hexane, then ethyl acetate gave a cream solid, which was crystallised from ethyl acetate to give the title compound as pale green crystals (0.18 g), m.p. 180-2°.

Workup

  1. temperaturerefluxed under nitrogen for 5 h
  2. extractionextracted with ethyl acetate (3×25 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b6921322051d43b49cf900e5ded90a2e
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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