HCID 68546473, compound → 2-Methyl-1-octyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one

HRID 1445934Notes

Reaction equation

HRID 1445934 reaction equation
C[O:2][C:3]1[C:8]2[CH:9]=[C:10]([CH3:20])[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]=2[CH:6]=[CH:5][N:4]=1>CC(O)=O.Br>[CH3:20][C:10]1[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]2[CH:6]=[CH:5][NH:4][C:3](=[O:2])[C:8]=2[CH:9]=1

Participants

4

Reactant 1

HCID 68546473HCID 68546473, compound

Product 1

HCID 685457012-Methyl-1-octyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Conditions

Temperature
105 °C

Procedure

To a stirred solution of 4-methoxy-2-methyl-1-octyl-1H-pyrrolo[3,2-c]pyridine 8 (0.22 g, 0.80 mmol) in AcOH (10 mL), 48% of HBr (5 mL) was added. The reaction mixture was heated to 105° C., and then stirred for 16 h, cooled to room temperature and evaporated. The obtained residue was dissolved in CH2Cl2 (80 mL), washed with saturated NaHCO3 (30 mL), brine (30 mL), dried over Na2SO4 and evaporated to afford crude product 9, which was used without further purification for next step. Yield: 207 mg (100%).

Workup

  1. temperaturecooled to room temperature
  2. customevaporated
  3. dissolutionThe obtained residue was dissolved in CH2Cl2 (80 mL)
  4. washwashed with saturated NaHCO3 (30 mL), brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-51ab888415d14f0585ba889592fd9047
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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