Water → 6-Benzyl-1, 7-dimethyl-4-nitro-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

HRID 628456Notes

Reaction equation

HRID 628456 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:16]=[C:15]([CH3:17])[NH:14][C:8]=3[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]2=[N:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([N:14]1[C:8]2[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[C:7]=2[CH:16]=[C:15]1[CH3:17])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 1369631061,7-Dimethyl-4-nitro-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 1181594136-Benzyl-1, 7-dimethyl-4-nitro-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1,7-dimethyl-4-nitro-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (0.30 g, 1.3 mmol, from Step 1) in N,N-dimethylformamide (5 mL) was added Cs2CO3 (0.51 g, 1.6 mmol). After stirring for 1 hour, benzyl bromide (0.18 mL, 1.6 mmol, Aldrich) was added, and the reaction mixture was stirred overnight, after which time water was added, and the reaction mixture was stirred for 5 minutes. Ethyl acetate was added, and the mixture was stirred overnight. The product, which had precipitated, was isolated by filtration. The product was washed sequentially with ethyl acetate, water, and again with ethyl acetate. Yield: (0.20 g, 48%). LCMS (M+H)+: 322.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. stirringthe reaction mixture was stirred for 5 minutes
  3. stirringthe mixture was stirred overnight
  4. customThe product, which had precipitated
  5. customwas isolated by filtration
  6. washThe product was washed sequentially with ethyl acetate, water

Sources & evidence

ORD record
ord-89bf61e810e64a98ac5cc67c7cb667ee
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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