Potassium Carbonate → HCID 59305015, compound

HRID 2240227Notes

Reaction equation

HRID 2240227 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:3]=1.[CH3:22]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:22][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 593050043-Bromo-4-nitro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59305015HCID 59305015, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 80 mg (210 μmol) of 3-bromo-4-nitro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine, 27 mg (210 μmol) of trimethylboroxine, 25 mg (20 μmol) of tetrakis(tri-phenylphosphine)palladium and 103 mg (640 μmol) of potassium carbonate in 2.00 ml of degassed DMF is stirred in a sealed pressure vessel at 110° C. for 6 h and then at RT overnight. The suspension is then filtered through an Extrelut silica gel cartridge, the cartridge is washed with a mixture of dichloromethane/methanol 1:1 and the filtrate is concentrated under reduced pressure. The residue is purified by preparative RP-HPLC.

Workup

  1. customat RT
  2. customovernight
  3. filtrationThe suspension is then filtered through an Extrelut silica gel cartridge
  4. washthe cartridge is washed with a mixture of dichloromethane/methanol 1:1
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-a924abc154f648538910d9126e40bab4
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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