Sodium Methoxide → HCID 117987733, compound

HRID 2206044Notes

Reaction equation

HRID 2206044 reaction equation
Cl[CH:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[C:5]([C:16]([O:18][CH3:19])=[O:17])=[CH:4][NH:3]1.[CH3:20][O-:21].[Na+]>CO>[CH:11]1([N:10]2[C:6]3[C:5]([C:16]([O:18][CH3:19])=[O:17])=[CH:4][NH:3][CH:2]([O:21][CH3:20])[C:7]=3[CH:8]=[CH:9]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 117988056HCID 117988056, compound

Product 1

HCID 117987733HCID 117987733, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-chloro-1-cyclopentyl-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (1.37 g) in methanol (5 mL) was added sodium methoxide (28% methanol solution, 5 mL), and the mixture was stirred at 70° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, to the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (879 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
  2. additionwas added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a466c16da88a405085fa7ca994270dcf
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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