1-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid methyl amide → 1-[1-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrol-2-yl]-propan-1-one

HRID 646248Notes

Reaction equation

HRID 646248 reaction equation
CN[C:3]([C:5]1[N:6]([CH2:20][CH3:21])[CH:7]=[C:8]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:9]=1)=[O:4].[CH3:22][CH2:23][Mg+].[Br-]>C1COCC1>[CH2:20]([N:6]1[CH:7]=[C:8]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:9]=[C:5]1[C:3](=[O:4])[CH2:22][CH3:23])[CH3:21]

Participants

4

Reactant 2

HCID 686995231-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid methyl amideHCID 178461630HCID 178461630, compound

Product 1

HCID 686988131-[1-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrol-2-yl]-propan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere to a cold (0° C.) solution of 1-ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid methyl amide (2.48 g, 7.93 mmol) in THF (40 ml) was added EtMgBr solution (1 molar in THF, 16 mL) over 10 minutes. The mixture was allowed to warm to room temperature and stirred for 18 hours, then poured into ice/1 N HCl solution and extracted with ether. The combined ether extracts were washed with brine, dried over MgSO4 and evaporated to dryness. The resultant residue was purified by flash chromatography (hexane/ethyl acetate 9.5/0.5) to give the title compound as an off white solid (1.8 g, 80% yield), mp 64° C., 1H NMR (400 MHZ, CDCl3) δ 1.16 (t, 3H), 1.35 (t, 3H), 2.8 (q, 2H), 3.79 (s, 3H), 4.35 (q 2H), 6.85 (m, 1H), 6.99-7.03 (m, 2H), 7.05 (m, 2H), 7.08 (m, 1H), MS m/e (M+H)+ 282.1.

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe resultant residue was purified by flash chromatography (hexane/ethyl acetate 9.5/0.5)

Sources & evidence

ORD record
ord-09e7833062474f83a242614dadeee947
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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