Pyridine → HCID 67341813, compound

HRID 1910845Notes

Reaction equation

HRID 1910845 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[S:15])[NH2:14])[CH:10]=[N:9]2)=[CH:5][CH:4]=1.Br[CH2:19][C:20](=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22].N1C=CC=CC=1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[S:15][CH:19]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:14]=3)[CH:10]=[N:9]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 66144Ethyl bromopyruvateHCID 86674816HCID 86674816, compound

Product 1

HCID 67341813HCID 67341813, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

According to Scheme 1 Step 5: A solution of 1-(4-methoxybenzyl)-1H-pyrazole-4-carbothioamide (26.7 mmol, 6.60 g), ethyl 3-bromo-2-oxopropanoate (29.4 mmol, 4.62 mL) and pyridine (29.4 mmol, 2.37 mL) in acetone (53 mL) was stirred at room temperature for 2 hours and at 45° C. for 52 hours. After evaporation, the crude residue was partitioned between EtOAc and a saturated solution of Na2CO3. The aqueous phase was extracted with EtOAc and then with DCM. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude residue was purified by flash chromatography over silica gel using DCM/EtOAc (100:0 to 70:30) to yield ethyl 2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazole-4-carboxylate (15.4 mmol, 5.28 g, 58%) as a dark oil.

Workup

  1. customAfter evaporation
  2. customthe crude residue was partitioned between EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure
  8. customThe crude residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-37a439abb86048e2a3b424db0b1502e5
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

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