alpha-Chloro-m-nitrotoluene → HCID 118159602, compound

HRID 628266Notes

Reaction equation

HRID 628266 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[NH:13][C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1.Cl[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=1>CN(C=O)C>[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[N:13]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=4)[C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1

Participants

5

Reactant 3

HCID 12078alpha-Chloro-m-nitrotolueneHCID 24758Sodium hydrideHCID 1369631111,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 118159602HCID 118159602, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.011 g, 0.27 mmol, 60% in mineral oil) was added to a solution of 1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (50.0 mg, 0.268 mmol, from Example 2, Step 5) in DMF (6 mL). After stirring for 10 minutes, 1-(chloromethyl)-3-nitro-benzene, (0.058 g, 0.34 mmol, Aldrich) was added. After stirring for 45 minutes, the reaction was quenched by the addition of water and the mixture was diluted with MeCN, filtered and purified via preparative HPLC-MS to afford product as a yellow solid (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.065 g, 75%).

Workup

  1. stirringAfter stirring for 45 minutes
  2. customthe reaction was quenched by the addition of water
  3. additionthe mixture was diluted with MeCN
  4. filtrationfiltered
  5. custompurified via preparative HPLC-MS
  6. customto afford product as a yellow solid (Waters XBridge C18
  7. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.065 g, 75%)

Sources & evidence

ORD record
ord-d1316d6d93324dd0b6f42156bf2281fa
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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