Diisopropylamine → [4-(3-Methoxyprop-1-ynyl)benzofuran-7-yl]amine

HRID 347322Notes

Reaction equation

HRID 347322 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].I[C:9]1[C:14]2[CH:15]=[CH:16][O:17][C:13]=2[C:12]([NH2:18])=[CH:11][CH:10]=1.[C:19](OCC)(=[O:21])C>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.[Cu](I)I>[CH3:19][O:21][CH2:2][C:1]#[C:3][C:9]1[C:14]2[CH:15]=[CH:16][O:17][C:13]=2[C:12]([NH2:18])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 210827234-Iodo-7-benzofuranamine

Product 1

HCID 21082722[4-(3-Methoxyprop-1-ynyl)benzofuran-7-yl]amine

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Bis(Triphenyl-phosphine)palladium(II) chloride (144 mg), copper iodide (58 mg) and diisopropylamine (208 mg) were added to a stirred solution of (4-Iodo-7-amino-benzfuran) (266 mg) and methyl propargyll ether (144 mg) in ethyl acetate (5 mls) at −20° C. The reaction was allowed to warm to ambient temperature over 16 hours. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3. The organics were washed with saturated NaHCO3, water and saturated brine and dried over magnesium sulfate. The product was purified by column chromatography on silica using 100% dichloromethane as eluent. [4-(3-methoxyprop-1-ynyl)benzofuran-7-yl]amine was thus obtained as a yellow/brown gum (70 mg); NMR Spectrum: (DMSOd6) 3.34 (s, 3H), 4.34 (s, 2H), 5.74 (s, 2H), 6.50 (d, 1H), 6.80 (s, 1H), 7.05 (d, 1H), 7.96, s, 1H); Mass Spectrum: M+H+ mass ion not observed.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3
  2. washThe organics were washed with saturated NaHCO3, water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe product was purified by column chromatography on silica using 100% dichloromethane as eluent

Sources & evidence

ORD record
ord-37ac8b37f06a473e8e4a73313b8c8d6c
Source dataset
uspto-grants-2007_02
Patent number
US07173136B2

Reaction notes

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