Sodium Carbonate → HCID 22462549, compound

HRID 1936715Notes

Reaction equation

HRID 1936715 reaction equation
Br[C:2]1[C:3]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[N:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[N+:11]([C:9]1[CH:8]=[CH:7][C:4]2[S:5][CH:6]=[C:2]([C:17]3[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=3)[C:3]=2[CH:10]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 166396973-Bromo-5-nitro-1-benzothiophene

Product 1

HCID 22462549HCID 22462549, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 3-bromo-5-nitrobenzo[b]thiophene (J.Amer. Chem. Soc, 1948, 1955) (4.2 g, 0.016 mole,) pyridin-4-ylboronic acid (2.0 g, 0.016 mole) and sodium carbonate (4.3 g, 0.048 mole) in DME (150 ml) and water (150 ml) was de-gassed by bubbling argon through for 15 minutes, then tetrakis(triphenylphosphine)palladium (0) (400 mg) was added and the mixture heated at reflux under argon for 18 hours. The reaction mixture was cooled and concentrated in vacuo to approx 150 ml volume, then acidified with 2M HCl acid (200 ml) and shaken well with ethyl acetate (400 ml). The solid present was filtered off, shaken with 10% Na2CO3 solution and dichloromethane, and the organic layer separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound as an orange/yellow solid (2.3 g, 56%).

Workup

  1. customwas de-gassed
  2. customby bubbling argon through for 15 minutes
  3. additiontetrakis(triphenylphosphine)palladium (0) (400 mg) was added
  4. temperaturethe mixture heated
  5. temperatureat reflux under argon for 18 hours
  6. temperatureThe reaction mixture was cooled
  7. concentrationconcentrated in vacuo to approx 150 ml volume
  8. filtrationThe solid present was filtered off
  9. stirringshaken with 10% Na2CO3 solution and dichloromethane
  10. customthe organic layer separated
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-238470c4d64341c9be3361bb96f613d0
Source dataset
uspto-grants-2002_05
Patent number
US06391891B1

Reaction notes

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