Stannous chloride dihydrate → HCID 69021256, compound

HRID 1865083Notes

Reaction equation

HRID 1865083 reaction equation
O.O.[Sn](Cl)Cl.[CH2:6]([O:8][C:9]([C:11]1[N:12]([CH3:35])[C:13]([CH2:33][CH3:34])=[C:14]([C:31]#[N:32])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:18][CH:17]=1)=[O:10])[CH3:7]>C(O)C>[CH2:6]([O:8][C:9]([C:11]1[N:12]([CH3:35])[C:13]([CH2:33][CH3:34])=[C:14]([C:31]#[N:32])[C:15]=1[C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:20][CH:21]=1)=[O:10])[CH3:7]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69021544HCID 69021544, compound

Product 1

HCID 69021256HCID 69021256, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Add tin (II) chloride dihydrate (669 mg, 3.54 mmol) into a solution of 3-[4-(3-nitro-pyridin-2-yl)-phenyl]-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (275 mg, 0.681 mmol, prepared in example E-38) in ethanol. Heat the mixture at 90° C. for 3 hours. Concentrate the reaction to remove ethanol. Dilute the residue with methylene chloride and H2O. Adjust the pH to 8 by adding saturated aqueous NaHCO3 solution. Extract with methylene chloride (2×30 mL) and EtOAc (2×30 mL). Combine the organic extracts, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography (elution with 17% acetone in hexanes) to provide the title compound as yellow solid (153 mg, 0.409 mmol, 60%). Mass spectrum (m/e): 375.1 (M+1). Rf=0.1 (17% of acetone in hexanes).

Workup

  1. concentrationConcentrate
  2. customthe reaction
  3. customto remove ethanol
  4. additionDilute the residue with methylene chloride and H2O
  5. additionby adding saturated aqueous NaHCO3 solution
  6. extractionExtract with methylene chloride (2×30 mL) and EtOAc (2×30 mL)
  7. dry with materialCombine the organic extracts, dry over anhydrous magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under reduced pressure
  10. customPurify the residue
  11. washby flash chromatography (elution with 17% acetone in hexanes)

Sources & evidence

ORD record
ord-0feb97db8f2c44cf9bfe94f07b1565fe
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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