Sodium ethoxide → HCID 68752272, compound

HRID 624161Notes

Reaction equation

HRID 624161 reaction equation
C([O-])C.[Na+].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:17]3[NH:18][CH:19]=[CH:20][CH:21]=3)=[N:15][N:16]=2)=[CH:8][CH:7]=1.ClCCl.CO>C(O)C>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:18]3[CH:19]=[CH:20][CH:21]=[C:17]3[C:14](=[O:13])[NH:15][N:16]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxide2×HCID 21226129Dichloromethane methanolHCID 136377377HCID 136377377, compound

Product 1

HCID 68752272HCID 68752272, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.469 g sodium ethanolate (6.89 mmol) dissolved in 20 ml ethanol was added 1.0 g 2-(4-bromophenyl)-5-(1H-pyrrol-2-yl)-1,3,4-oxadiazole (3.45 mmol) at room temperature under nitrogen and the mixture was stirred at room temperature for 5 minutes. The reaction was heated at 160° C. for 2 hours in a microwave (Biotage Initiator 2.5). The reaction was monitored by TLC dichloromethane/methanol=9/1. Additional equivalents of sodium ethanolate were added and additional heating was carried out until completion of the reaction according to TLC. The reaction mixture was concentrated under reduced pressure and adsorbed on silica gel. The product was purified by silica gel chromatography (gradient: cyclohexane/ethylacetate=0-100%) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 12.09 (s, 1H), 7.85-7.78 (m, 2H), 7.76-7.69 (m, 2H), 7.39 (dd, J=1.3, 2.9, 1H), 7.16 (dd, J=1.4, 3.8, 1H), 6.77 (dd, J=2.9, 3.8, 1H). 13C NMR (400 MHz, DMSO-d6) δ 154.22, 136.46, 131.98, 130.90, 129.52, 124.07, 124.00, 118.80, 114.42, 111.01.

Workup

  1. temperatureadditional heating
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe product was purified by silica gel chromatography (gradient: cyclohexane/ethylacetate=0-100%)

Sources & evidence

ORD record
ord-1ad52147642e43debd8df69445fbae35
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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