5-Bromothiophene-2-carbaldehyde → HCID 57423164, compound

HRID 2114617Notes

Reaction equation

HRID 2114617 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[NH2:10].[Br:11][C:12]1[S:16][C:15]([CH:17]=O)=[CH:14][CH:13]=1.[BH4-].[Na+]>CCO.CO>[Br:11][C:12]1[S:16][C:15]([CH2:17][NH:10][C:3]2[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=2[F:1])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 784285-Bromothiophene-2-carbaldehydeHCID 949532,4,5-TrifluoroanilineHCID 4311764Sodium borohydride

Product 1

HCID 57423164HCID 57423164, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 2 g (13.6 mmol) of 2,4,5-trifluorophenylamine and 2.66 g (13.9 mmol) of 5-bromothiophene-2-carbaldehyde in 30 ml of EtOH, 9.4 g of molecular sieves (0.3 nm) were added and the mixture was refluxed for 20 hours. After this time the reaction mixture was cooled to room temperature, filtered and the solvent was evaporated in vacuo. The oil obtained was dissolved in 30 ml of MeOH and 0.51 g (13.6 mmol) of NaBH4 were added in small portions, maintaining the temperature of the reaction at room temperature. The mixture was stirred at this temperature for 20 more hours. After this time the solvent was evaporated in vacuo and the residue was treated with 100 ml of water and extracted twice with ether. The organic layers were combined, washed with brine, dried over anhydrous MgSO4, filtered and evaporated to dryness to give 3.2 g of an oil. This 3.2 g were combined with 3.5 g obtained in a subsequent preparation and the total product obtained (6.7 g) was purified by chromatography on silica gel using mixtures of hexane/AcOEt 5:1→1:1 as eluent Appropriate fractions were combined to give 0.95 g of the title product as an oil. (global yield 8.2%).

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. filtrationfiltered
  3. customthe solvent was evaporated in vacuo
  4. customThe oil obtained
  5. temperaturemaintaining
  6. customthe temperature of the reaction at room temperature
  7. customAfter this time the solvent was evaporated in vacuo
  8. additionthe residue was treated with 100 ml of water
  9. extractionextracted twice with ether
  10. washwashed with brine
  11. dry with materialdried over anhydrous MgSO4
  12. filtrationfiltered
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-f3936da4ea7c409880564a2c584de321
Source dataset
uspto-grants-2008_10
Patent number
US07435742B2

Reaction notes

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