Stannous chloride dihydrate → HCID 57442269, compound

HRID 2079907Notes

Reaction equation

HRID 2079907 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=3)[N:10]([CH:20]([CH3:22])[CH3:21])[CH:9]=2)=[CH:6][C:5]([C:23]#[N:24])=[N:4]1)[CH3:2].O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16]([C:8]([C:7]3[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([C:23]#[N:24])[CH:6]=3)=[CH:9][N:10]2[CH:20]([CH3:21])[CH3:22])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 57442268HCID 57442268, compound

Product 1

HCID 57442269HCID 57442269, compoundYield 109.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stir a solution of 1-Ethyl-5-(1-isopropyl-6-nitro-1H-indol-3-yl)-1H-pyrazole-3-carbonitrile (0.127 g, 0.393 mmol) and tin(II) chloride dihydrate (0.887 g, 3.93 mmol) in DMF (2.5 mL) at 70° C. for 1 h. After this time, Pour the reaction carefully into a stirring solution of saturated aqueous sodium bicarbonate (50 mL), diluted with ethyl acetate (50 mL) and stir for 15 min. Filter the resulting mixture through diatomaceous earth. Separate the organic layer of the filtrate and wash with water (3×50 mL) then brine (50 mL). Dry the resulting solution over sodium sulfate, filtered and concentrate the filtrate under reduced pressure to afford 5-(6-Amino-1-isopropyl-1H-indol-3-yl)-1-ethyl-1H-pyrazole-3-carbonitrile (0.126 g, quant.) as a yellow foam. Use the foam without further purification.

Workup

  1. additionAfter this time, Pour
  2. filtrationFilter the resulting mixture through diatomaceous earth
  3. customSeparate the organic layer of the filtrate
  4. washwash with water (3×50 mL)
  5. dry with materialDry the resulting solution over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-3ee756e5325d44a5b2aadc7292009206
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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