o-Xylyl bromide → HCID 118159641, compound

HRID 628261Notes

Reaction equation

HRID 628261 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]=[CH:21][C:20]=1[CH3:25]>CN(C=O)C>[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 6992o-Xylyl bromideHCID 24758Sodium hydrideHCID 1369631111,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 118159641HCID 118159641, 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 (15.0 mg, 0.0806 mmol, from Example 2, Step 5) in DMF (2.2 mL) was added sodium hydride (0.0098 g, 0.24 mmol, 60% in mineral oil). After stirring for 10 minutes, 1-(bromomethyl)-2-methylbenzene (0.015 g, 0.080 mmol, Aldrich) was added. After stirring for 45 minutes, the reaction was quenched by the addition of water and diluted to 5 mL volume with MeCN. The solution was filtered and purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (9 mg, 40%).

Workup

  1. stirringAfter stirring for 45 minutes
  2. customthe reaction was quenched by the addition of water
  3. additiondiluted to 5 mL volume with MeCN
  4. filtrationThe solution was filtered
  5. custompurified by preparative HPLC-MS (Waters XBridge C18
  6. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (9 mg, 40%)

Sources & evidence

ORD record
ord-2c2341c1b6f84d13a168980ed46f57b0
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

Loading…