HCID 10198756, compound → HCID 178480211, compound

HRID 1075572Notes

Reaction equation

HRID 1075572 reaction equation
C[O:2][C:3]1[N:8]=[C:7]2[C:9]([CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:10][NH:11][C:6]2=[CH:5][CH:4]=1>Br.C(O)(=O)C>[OH:2][C:3]1[N:8]=[C:7]2[C:9]([CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:10][NH:11][C:6]2=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 10198756HCID 10198756, compound

Product 1

HCID 178480211HCID 178480211, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent2×

Procedure

A solution of 1.00 gm (4.1 mMol) 5-methoxy-3-(1-methyl-piperidin-4-yl)pyrrolo[3,2-b]pyridine in 20 mL hydrogen bromide (30% in acetic acid) was heated at reflux for 48 hours. Additional 5 mL aliquots of hydrogen bromide in acetic acid were added at about 8 and 24 hours. The reaction mixture was concentrated under reduced pressure and the residue treated with 1 mL saturated aqueous sodium bicarbonate. The resulting mixture was taken up in methanol and passed over a VARIAN BOND ELUT SCX™ (Varian, Harbor City, Calif., U.S.A.) ion exchange column which had been preactivated with 10% acetic acid in methanol. The column was washed with three volumes of methanol which were discarded, and then with methanol containing ammonia. Fractions containing product were combined and concentrated under reduced pressure to provide 0.892 gm (94%) of the title compound. An analytical sample was further subjected to flash silica gel chromatography, eluting with dichloromethane containing from 10-40% methanol. Fractions containing product were combined and concentrated under reduced pressure. The residue was crystallized from methanol.

Workup

  1. temperatureat reflux for 48 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue treated with 1 mL saturated aqueous sodium bicarbonate
  4. washThe column was washed with three volumes of methanol which
  5. additionwith methanol containing ammonia
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a159ee01c83047c09c1c99ec2077a57f
Source dataset
uspto-grants-1999_05
Patent number
US05905084

Reaction notes

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