Diethyl Ether → 2-(5-Bromo-2-methyl-3-thienyl)furo[3,2-c]imidazo[1,2-a]pyridine

HRID 376321Notes

Reaction equation

HRID 376321 reaction equation
[NH2:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[Br:11][C:12]1[S:16][C:15]([CH3:17])=[C:14]([C:18](=O)[CH2:19]Br)[CH:13]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC>O1CCCC1>[Br:11][C:12]1[S:16][C:15]([CH3:17])=[C:14]([C:18]2[N:1]=[C:2]3[C:7]4[CH:8]=[CH:9][O:10][C:6]=4[CH:5]=[CH:4][N:3]3[CH:19]=2)[CH:13]=1.[CH3:17][C:15]1[S:16][CH:12]=[CH:13][C:14]=1[C:18]1[N:1]=[C:2]2[C:7]3[CH:8]=[CH:9][O:10][C:6]=3[CH:5]=[CH:4][N:3]2[CH:19]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 186911695-Bromo-3-bromoacetyl-2-methylthiopheneHCID 21226445Aluminium lithium hydride2×HCID 22665882Furo[3,2-c]pyridin-4-amine

Product 2

HCID 186911162-(5-Bromo-2-methyl-3-thienyl)furo[3,2-c]imidazo[1,2-a]pyridineHCID 186912202-(2-Methyl-3-thienyl)furo[3,2-c]imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.1 g of 2-(5-bromo-2-methyl-3-thienyl)furo[3,2-c]imidazo[1,2-a]pyridine, which was prepared by the reaction of 4-aminofuro[3,2-c]pyridine and 5-bromo-3-bromoacetyl-2-methylthiophene in a similar manner to that of aforementioned Preparation 7, in 50 ml of tetrahydrofuran was added dropwise to a solution of 3.5 g of lithium aluminum hydride in 50 ml of tetrahydrofuran. When addition was complete, the mixture was refluxed for 2 hours. After being cooled, excessive lithium aluminum hydride was decomposed by the addition of hydrous ether, and the mixture was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure to give 4.5 g of the title compound as a white powder.

Workup

  1. customof aforementioned Preparation 7
  2. additionWhen addition
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperatureAfter being cooled
  5. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-15018166ec814c1f8868a717f8ff9118
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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