Hydrogen Bromide → 4-Bromothieno[3,2-C]pyridin-6-amine

HRID 1251180Notes

Reaction equation

HRID 1251180 reaction equation
[C:1]([CH2:3][C:4]1[S:5][CH:6]=[CH:7][C:8]=1[C:9]#[N:10])#[N:2].[BrH:11].[OH-].[Na+]>C(O)(=O)C>[NH2:2][C:1]1[N:10]=[C:9]([Br:11])[C:8]2[CH:7]=[CH:6][S:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 225034392-(Cyanomethyl)thiophene-3-carbonitrile

Product 1

HCID 225034234-Bromothieno[3,2-C]pyridin-6-amineYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Cyanomethyl-3-cyanothiophene (823 mg) was added to a solution (30 ml) of 25% hydrogen bromide in acetic acid, and the resulting mixture was stirred under ice-cooling for 90 min, which was neutralized with a 8N aqueous solution of sodium hydroxide and then extracted with ethyl acetate. The organic layer was washed with water, dried (over MgSO4) and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow solid (894 mg, yield; 70%).

Workup

  1. temperaturecooling for 90 min
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (over MgSO4)
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-2623786af7d6425c94c505bb58e434d5
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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