5-Bromo-2,4-dimethoxybenzaldehyde → HCID 21082509, compound

HRID 347367Notes

Reaction equation

HRID 347367 reaction equation
Br[C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:14][N:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[Sn](CCCC)(CCCC)CCCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][O:10][C:5]1[CH:4]=[C:3]([O:12][CH3:13])[C:2]([C:16]2[N:15]([CH3:14])[CH:19]=[CH:18][CH:17]=2)=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 2

HCID 6683465-Bromo-2,4-dimethoxybenzaldehydeHCID 27693971-methyl-2-(tributylstannyl)-1H-pyrrole

Product 1

HCID 21082509HCID 21082509, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ex-44A: A solution of 5-bromo-2,4-dimethoxybenzaldehyde (1.90 g, 7.77 mmol) and trans-dichlorobis(triphenylphosphine)palladium(II) in dioxane (150 mL) was treated with 1-methyl-2-(tributylstannyl)-1H-pyrrole and then refluxed for 68 h. The reaction mixture was quenched with 10% potassium fluoride/ether (300 mL/100 mL) and filtered through Celite. The organic phase was extracted with saturated ammonium chloride solution (4×25 mL), dried over magnesium sulfate, and concentrated to a brown solid. The solid was purified by column chromatography (30% ethyl acetate/hexane) to yield 0.87 g (46%) of 2,4-dimethoxy-5-(1-methyl-1H-pyrrol-2-yl)benzaldehyde as a white solid. 1H-NMR (300 MHz, CDCl3) δ 10.34 (s, 1 H), 7.78 (s, 1H), 6.72 (m, 1H), 6.51 (s, 1H), 6.20 (m, 1H), 6.13 (m, 1H), 4.01 (s, 3H), 3.92 (s, 3H), 3.46 (s, 3H).

Workup

  1. temperaturerefluxed for 68 h
  2. customThe reaction mixture was quenched with 10% potassium fluoride/ether (300 mL/100 mL)
  3. filtrationfiltered through Celite
  4. extractionThe organic phase was extracted with saturated ammonium chloride solution (4×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to a brown solid
  7. customThe solid was purified by column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7596513eada74e698d67c62cd73e5c2a
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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