Hydrochloric Acid → 3-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

HRID 2206045Notes

Reaction equation

HRID 2206045 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]([O:15][CH3:16])[NH:8][CH:9]=[C:10]([C:11]([O:13]C)=[O:12])[C:5]=2[N:4]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:3]=1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[C:6]2[CH:7]([O:15][CH3:16])[NH:8][CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:5]=2[N:4]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117987803methyl 3-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Product 1

HCID 1179880413-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acidYield 106.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (874 mg) in methanol (8 mL) was added 1N aqueous sodium hydroxide solution (8 mL), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added 1N hydrochloric acid at 0° C., and the precipitate was collected by filtration, and dried to give the title compound (894 mg).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-bb02cae836f34109975233a0c0ddded2
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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