Nitromethane → methyl 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate

HRID 1157787Notes

Reaction equation

HRID 1157787 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[N+](C)([O-])=O.[CH3:9][O:10][C:11]1[CH:16]=[N:15][C:14]([N:17]2[CH:21]=[N:20][C:19]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[N:18]2)=[C:13]2[NH:29][CH:30]=[CH:31][C:12]=12.Cl[C:33](=[O:38])[C:34]([O:36][CH3:37])=[O:35]>C(Cl)Cl>[CH3:9][O:10][C:11]1[CH:16]=[N:15][C:14]([N:17]2[CH:21]=[N:20][C:19]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[N:18]2)=[C:13]2[NH:29][CH:30]=[C:31]([C:33](=[O:38])[C:34]([O:36][CH3:37])=[O:35])[C:12]=12

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) ChlorideHCID 59511460N-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)pivalamide

Product 1

HCID 68694028methyl 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetateYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an oven-dried flask in ice bath was added AlCl3 (382 mg, 2.86 mmol), then CH2Cl2 (4 mL) was introduced at 0° C. Nitromethane (10.84 μL, 0.201 mmol) was added at that temperature. Ice bath was removed and the mixture was stirred at room temperature for 30 min. N-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)pivalamide (90 mg, 0.286 mmol) and methyl 2-chloro-2-oxoacetate (0.079 mL, 0.859 mmol) were added at 0° C. The reaction mixture was stirred for three hours at room temperature. The reaction mixture was quenched with ammonium acetate (8 mL) and extracted with ethyl acetate (3×10 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford methyl 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (40 mg, 45%) as white solid.

Workup

  1. customIce bath was removed
  2. stirringThe reaction mixture was stirred for three hours at room temperature
  3. customThe reaction mixture was quenched with ammonium acetate (8 mL)
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc15db54c3734dd284cef43d19172240
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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