Trifluoroacetic acid → 3-Bromo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

HRID 1930798Notes

Reaction equation

HRID 1930798 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][N:9](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:8][C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][NH:9][CH2:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 577536743-Bromo-6-trityl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Product 1

HCID 577535623-Bromo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 0.18 mmol 3-bromo-6-trityl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine in 0.5 ml chloroform and 0.5 ml methanol was added dropwise 1 ml trifluoroacetic acid. After 5 minutes stirring at 0° C. and 30 minutes at RT, the reaction mixture was concentrated. The residue was taken in water/ether and 1 ml 1N HCl was added. The aqueous phase was extracted with ether (2 times), then basified with 5N NaOH and extracted with dichloromethane (3 times). Combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as a light yellow solid. MS (m/e): 199.0 (M+, 100%)

Workup

  1. concentrationthe reaction mixture was concentrated
  2. addition1 ml 1N HCl was added
  3. extractionThe aqueous phase was extracted with ether (2 times)
  4. extractionextracted with dichloromethane (3 times)
  5. dry with materialCombined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-961169f4056f4d359ef3723eb4946444
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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