Benzyl Bromide → HCID 118159576, compound

HRID 628396Notes

Reaction equation

HRID 628396 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[NH:11][C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[C:18]([O-:21])([O-])=[O:19].[Cs+].[Cs+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.O.CO>[F:15][C:14]([F:17])([F:16])[C:18]([OH:21])=[O:19].[F:15][C:14]([F:17])([F:16])[C:18]([OH:21])=[O:19].[CH2:24]([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[C:14]([F:17])([F:15])[F:16])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 136963105HCID 136963105, compound

Product 1

HCID 118159576HCID 118159576, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-methyl-7-(trifluoromethyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (0.020 g, 0.083 mmol, from Step 4) in DMF (0.5 mL) was treated with Cs2CO3 (0.054 g, 0.17 mmol) and benzyl bromide (0.010 mL, 0.084 mmol, Aldrich). After stirring overnight, the reaction was diluted with water and MeOH. The product was purified by preparative HPLC-MS (Waters SunFire C18, eluting with a gradient of MeCN/H2O containing 0.1% TFA). Yield: (6 mg, 12%).

Workup

  1. customThe product was purified by preparative HPLC-MS (Waters SunFire C18
  2. washeluting with a gradient of MeCN/H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-4c31067debdb4e1f9706092d102b9a4a
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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