Diethyl Ether → 2-Chloro-3-methyl-7-(2-phenylethyl)pyrrolo[2,3-b]pyridine

HRID 1756047Notes

Reaction equation

HRID 1756047 reaction equation
[Cl:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11].Br[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCOCC.C(OCC)(=O)C>C(#N)C.CO.C(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:5]2[N:6]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 7666Phenethyl bromideHCID 8857Ethyl AcetateHCID 193925862-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 199167992-Chloro-3-methyl-7-(2-phenylethyl)pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.1 g (0.6 mmol) 2-chloro-3-methylpyrrolo-[2,3-b]pyridine and 0.14 g (0.78 mmol) (2-bromoethyl)-benzene in 10 ml acetonitril was refluxed 72 h. The solvent was evaporated. The solid that formed was treated with ether and ethyl acetate and isolated by filtration. Chromatography on silica gel eluting with methylene chloride and methanol (10:1) gave the desired product. (0.03 g 18% ).

Workup

  1. customThe solvent was evaporated
  2. customThe solid that formed
  3. customisolated by filtration

Sources & evidence

ORD record
ord-d8291cf468cb42cb8ec1469939137576
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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