Dimethylformamide → HCID 89648676, compound

HRID 1484673Notes

Reaction equation

HRID 1484673 reaction equation
NC1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:3]=1.[H-].[Li+].IC.[CH3:24][N:25]([CH:27]=O)[CH3:26]>>[CH3:26][N:25]([CH3:24])[C:27]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 62714Lithium hydrideHCID 11391384ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 89648676HCID 89648676, compound

Procedure

1.96 g of ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate 1-8-1 (7.46 mmol, 1.0 eq.) were dissolved in 9.8 mL of dry DMF. Under nitrogen atmosphere 237 mg of lithium hydride (29.8 mmol, 4.0 eq.) were added at 0° C. bath temperature. The mixture was stirred for one hour at this temperature. Then 3.7 mL of iodomethane (59.6 mmol, 8.0 eq.) were added at 0° C. bath temperature. The reaction mixture was stirred then for three days at rt. After the addition of ice it was stirred for 30 minutes and then extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography to provided 1.35 g (4.49 mmol, 60%) of analytically pure target compound.

Workup

  1. stirringThe reaction mixture was stirred
  2. waitfor three days at rt
  3. additionAfter the addition of ice it
  4. stirringwas stirred for 30 minutes
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. customto provided 1.35 g (4.49 mmol, 60%) of analytically pure target compound

Sources & evidence

ORD record
ord-78d9764a009a421b9c26009683db7579
Source dataset
uspto-grants-2016_08
Patent number
US09422268B2

Reaction notes

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