Tetrahydrofuran → HCID 67356355, compound

HRID 1478905Notes

Reaction equation

HRID 1478905 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]=2[N:4]([CH3:15])[CH:3]=1.C1COCC1>>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[N:4]([CH3:15])[CH:3]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 67353376HCID 67353376, compound

Product 1

HCID 67356355HCID 67356355, compoundYield 91%

Procedure

In a 200 ml round bottom flask, methyl 3-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (3E, 8.5 g, 32 mmol) was dissolved THF (50 ml) NaOH (32 ml, 63 mmol) solution was added to the mixture and the stirring continued at room temperature overnight. Another equivalent of base was added and the mixture was warmed with water bath to complete the reaction. Volatiles were removed in vacuo and the residue was cooled in an ice bath and neutralized with dilute HCl to pH 4.0-4.5. The precipitated product was collected by filtration to give the product 3-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (3F, 7.3 g, 91%).

Workup

  1. additionwas added to the mixture
  2. additionAnother equivalent of base was added
  3. temperaturethe mixture was warmed with water bath
  4. customthe reaction
  5. customVolatiles were removed in vacuo
  6. temperaturethe residue was cooled in an ice bath
  7. filtrationThe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-d8d698cb77c940edbc08b1b2e856cbbb
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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