Sodium hydride → HCID 118159718, compound

HRID 628262Notes

Reaction equation

HRID 628262 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[NH:11][C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1>CN(C=O)C>[CH3:26][O:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][N:11]1[C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[C:7]=2[CH:13]=[C:12]1[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 40672073-Methoxybenzyl bromideHCID 1369631111,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 118159718HCID 118159718, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 (4 mL) was added sodium hydride (0.032 g, 0.81 mmol, 60% in mineral oil). After stirring for 10 minutes, 1-(bromomethyl)-3-methoxybenzene (0.038 mL, 0.27 mmol, Aldrich) was added and the reaction was stirred for 45 minutes and was quenched by the addition of water and diluted with MeCN, filtered and purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.04 g, 50%).

Workup

  1. stirringthe reaction was stirred for 45 minutes
  2. customwas quenched by the addition of water
  3. additiondiluted with MeCN
  4. filtrationfiltered
  5. custompurified by preparative HPLC-MS (Waters XBridge C18
  6. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.04 g, 50%)

Sources & evidence

ORD record
ord-48ccde2f1d47428e86933804a5a882ca
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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