Nitrogen → HCID 22025594, compound

HRID 396594

Reaction equation

HRID 396594 reaction equation
N#N.Br[C:4]1[C:5]([O:13][CH3:14])=[CH:6][C:7]([OH:12])=[C:8]([CH:11]=1)[CH:9]=[O:10].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[S:15]1[C:19]([C:4]2[C:5]([O:13][CH3:14])=[CH:6][C:7]([OH:12])=[C:8]([CH:11]=2)[CH:9]=[O:10])=[CH:18][C:17]2[CH:5]=[CH:4][CH:11]=[CH:8][C:16]1=2

Participants

6

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 8181085-Bromo-2-hydroxy-4-methoxybenzaldehydeHCID 27339602-Thiopheneboronic acid

Product 1

HCID 22025594HCID 22025594, compoundYield 170.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Ex-62B: A stream of N2 was bubbled through a solution of 5-bromo-2-hydroxy-4-methoxybenzaldehyde (1 g, 4.3 mmol) from Ex-62A in 30 mL of ethylene glycol dimethyl ether for 15 min. Tetrakis-triphenylphosphine palladium (0) (0.5 g, 0.4 mmol) was added along with thiophene-2-boronic acid (1.2 g, 6.5 mmol) and 10 mL of Na2CO3 (2M aqueous solution). The resulting mixture was stirred under reflux overnight. The solvent was removed by rotary evaporation and the residue was treated with saturated NaHCO3 and extracted with dichloromethane. The organic phase was washed with brine, dried over MgSO4, and filtered to remove drying agent. Solvent was removed by rotary evaporation. Purification of the crude material by silica gel chromatography (hexanes/EtOAc, 2:1) gave 1.04 g of the desired 5-benzo[b]thien-2-yl-2-hydroxy-4-methoxybenzaldehyde.

Workup

  1. temperatureunder reflux overnight
  2. customThe solvent was removed by rotary evaporation
  3. additionthe residue was treated with saturated NaHCO3
  4. extractionextracted with dichloromethane
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customto remove
  9. customdrying agent
  10. customSolvent was removed by rotary evaporation
  11. customPurification of the crude material by silica gel chromatography (hexanes/EtOAc, 2:1)

Sources & evidence

ORD record
ord-6d24c9270c8444baa03a6173ce021793
Source dataset
uspto-grants-2003_08
Patent number
US06608101B1

Linked notes

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