Hexane → HCID 59772707, compound

HRID 646266Notes

Reaction equation

HRID 646266 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[NH:5][CH:6]=1.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[CH:17])[CH:11]=1.C(N(CC)CC)C.CCCCCC>CN(C=O)C.O.[Cu](I)I.C(OCC)(=O)C>[Br:9][C:10]1[CH:11]=[C:12]([C:16]#[C:17][C:2]2[CH:3]=[C:4]([CH:7]=[O:8])[NH:5][CH:6]=2)[CH:13]=[CH:14][CH:15]=1

Participants

9

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 46719534-iodo-1H-pyrrole-2-carbaldehydeHCID 114808181-Bromo-3-ethynylbenzene

Product 1

HCID 59772707HCID 59772707, compoundYield 93.5%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-iodo-1H-pyrrole-2-carbaldehyde (0.50 g; 2.262 mmol) and bis(triphenylphosphine)palladium-(II)chloride (0.079 g; 0.113 mmol)) in DMF (15 mL; degassed with nitrogen for 30 minutes) was stirred at ambient temperature for 15 minutes. Then the following were added: 1-bromo-3-ethynylbenzene (0.61 g; 3.394 mmol), copper iodide (43 mg; 0.226), and triethylamine (1.58 mL, 11.3 mmol). The course of the reaction was followed with TLC (4:1, hexane:ethyl acetate). After 2 hours the reaction mixture was diluted with water and the organic material was extracted into dichloromethane. The organic extracts were washed with water and brine, dried over MgSO4, filtered, and evaporated. The residue was chromatographed on silica gel using 3:1 hexane:ethyl acetate to yield 0.58 g (93%) of the title compound as a yellow crystalline solid, mp 152-156° C.; MS (ES) m/z 272.0, [M−H]−.

Workup

  1. additionThen the following were added
  2. extractionthe organic material was extracted into dichloromethane
  3. washThe organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica gel using 3:1 hexane

Sources & evidence

ORD record
ord-a916635bf71d41eb9946a3191956a677
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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