Ethyl Acetate → HCID 67333040, compound

HRID 1886962Notes

Reaction equation

HRID 1886962 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](Cl)(=[O:21])[CH:18]([CH3:20])[CH3:19].C(OCC)(=O)C>N1C=CC=CC=1>[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[CH:12][C:10]=3[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 62325Isobutyryl chlorideHCID 167651722-Phenyl-1-benzofuran-5-amine

Product 1

HCID 67333040HCID 67333040, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-phenylbenzofuran-5-amine (210 mg, 1.00 mmol) in pyridine (5 mL) at room temperature was added isobutyryl chloride (120 μL, 1.10 mmol). The resulting mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic layer was washed with saturated aqueous copper sulfate solution followed by saturated aqueous potassium carbonate solution. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting material was purified by column chromatography eluting using a gradient (ethyl acetate/hexanes 1:3 v/v to ethyl acetate/hexanes 1:2 v/v) to afford 134 mg (48%) of the title compound (LCMS RT=6.81 min, MH+ 280.1)

Workup

  1. washthe organic layer was washed with saturated aqueous copper sulfate solution
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. customevaporated
  4. customThe resulting material was purified by column chromatography
  5. washeluting

Sources & evidence

ORD record
ord-5a589535934440bb8b5a494fea631b53
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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