Phenacyl bromide → HCID 19916779, compound

HRID 1756090Notes

Reaction equation

HRID 1756090 reaction equation
[C:1]([CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:3])[NH2:2].[CH2:20](Br)[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>C(#N)C.CO.C(Cl)Cl>[C:1]([CH2:4][C:5]1[C:13]2[C:8]([N:9]([CH2:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:22])[CH:10]=[CH:11][CH:12]=2)=[N:7][C:6]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:3])[NH2:2]

Participants

6

Reactant 2

HCID 6259Phenacyl bromideHCID 22477388HCID 22477388, compound

Product 1

HCID 19916779HCID 19916779, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-(Carbamoylmethyl)-2-phenylpyrrolo[2,3-b]pyridine (0.35 g, 1.4 mmol) and phenacyl bromide (0.33 g) in acetonitrile (5 ml) were refluxed under argon for 3 h. The resulting yellow suspension was isolated by filtration (0.4 g). The sparingly soluble raw product was dissolved in a mixture of methanol (20 ml) and methylene chloride (480 ml), loaded on a flash chromatography column (SiO2 /CH2Cl2 :MeOH 96:4), and eluted with a) 1000 ml MeOH:CH2Cl2 2.5:97.5; b) 1000 ml MeOH:CH2Cl2 5:95; c) 1000 ml MeOH:CH2Cl2 1:9 to afford pure 3-(carbamoylmethyl)-7-phenacyl-2-phenylpyrrolo[2,3-b]pyridine which was isolated as its hydrobromide (0.14 g, 22%).

Workup

  1. customThe resulting yellow suspension was isolated by filtration (0.4 g)
  2. washeluted with a) 1000 ml MeOH:CH2Cl2 2.5:97.5

Sources & evidence

ORD record
ord-389fb3180e994fad918e4b1b57d3c04f
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

Loading…