Potassium Carbonate → 6-bromo-1-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1H-pyrrolo[3,2-b]pyridine

HRID 1404579Notes

Reaction equation

HRID 1404579 reaction equation
CS([O:5][CH:6]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=1[Cl:16])[CH3:7])(=O)=O.[Br:17][C:18]1[CH:19]=[C:20]([N+:35]([O-])=O)[C:21]([CH:24](C(OCC)=O)[C:25](OCC)=O)=[N:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:17][C:18]1[CH:19]=[C:20]2[N:35]([O:5][CH:6]([C:8]3[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=3[Cl:16])[CH3:7])[CH:25]=[CH:24][C:21]2=[N:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57516275HCID 57516275, compoundHCID 585324961-(2,6-Dichloro-3-fluorophenyl)ethyl methanesulfonate

Product 1

HCID 674584186-bromo-1-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1H-pyrrolo[3,2-b]pyridineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2,6-dichloro-3-fluorophenyl)ethyl methanesulfonate (4.39 g, 15.3 mmol, 1.0 eq), 6-bromo-1H-pyrrolo[3,2-b]pyridin-1-ol (prepared as in example 1: 3.92 g, 20.0 mmol, 1.3 eq) and K2CO3 (6.34 g, 45.9 mmol, 3.0 eq) in 90 ml of N,N-dimethylformamide (DMF) was stirred at room temperature overnight. The solid was filtered out and the solvent evaporated. The residue was dissolved in DCM, and the solution was washed with water and brine, dried, evaporated and chromatographed (MeOH/DCM 1:20) to give a light yellow oil, 4.63 g, in 78% yield.

Workup

  1. filtrationThe solid was filtered out
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. washthe solution was washed with water and brine
  5. customdried
  6. customevaporated
  7. customchromatographed (MeOH/DCM 1:20)
  8. customto give a light yellow oil, 4.63 g

Sources & evidence

ORD record
ord-b14a655b409c405baae399dddaf72956
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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