(1-Bromoethyl)benzene → HCID 178463349, compound

HRID 502795Notes

Reaction equation

HRID 502795 reaction equation
[C:1]1([C:7]2[NH:16][C:10]3=[N:11][CH:12]=[C:13]([NH2:15])[CH:14]=[C:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH:23](Br)[CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[C:17]1([CH:23]([NH:15][C:13]2[CH:14]=[C:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[NH:16][C:10]3=[N:11][CH:12]=2)[CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 11454(1-Bromoethyl)benzeneHCID 178508009HCID 178508009, compound

Product 1

HCID 178463349HCID 178463349, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg 2-phenyl-3H-imidazo[4,5-b]pyridin-6-ylamine from ex. b) were dissolved in 1 mL dry dimethylformamide (DMF) and 92 mg 1-phenylethyl bromide were added at room temperature. The mixture was stirred for 18 hours (hrs), the DMF was removed under vacuum and the residue purified by chromatography on silica eluting stepwise first with dichloromethane, then dichloromethane/methanol (60:1), then dichloromethane/methanol/ammonia (60:1:0,2). Product containing fractions were pooled and further purified by preparative HPLC-MS.

Workup

  1. customthe DMF was removed under vacuum
  2. customthe residue purified by chromatography on silica eluting stepwise first with dichloromethane
  3. additionProduct containing fractions
  4. customfurther purified by preparative HPLC-MS

Sources & evidence

ORD record
ord-618a244c729840fa9bdca0abad939ede
Source dataset
uspto-grants-2010_08
Patent number
US07776878B2

Reaction notes

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