Methanol → HCID 22047369, compound

HRID 1830561Notes

Reaction equation

HRID 1830561 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:13]([Br:14])=[CH:12][S:11][C:8]2=[CH:9][N:10]=1)=[O:4].CO.[OH-].[Na+]>O>[Br:14][C:13]1[C:7]2[C:8](=[CH:9][N:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 69362025478149-32-5

Product 1

HCID 22047369HCID 22047369, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl-3-bromothieno[2,3-c]pyridine-5-carboxylate (635 mg, 2.33 mmol) is combined with 25 ml MeOH. The mixture is treated with 2N NaOH (3 ml, 6 mmole) and 3 ml H2O and the reaction is stirred 4 h at rt. The volatiles are removed in vacuo and the residue is combined with 5 ml H2O. The pH of the mixture is adjusted to 3.5 with 10% aqueous HCl. The tan precipitate is collected, washed with water, and is dried in vacuo at 50° C. to afford 475 mg (79%) of 3-bromothieno[2,3-c]pyridine-5-carboxylic acid as a tan solid. MS (ESI): 257.9.

Workup

  1. customThe volatiles are removed in vacuo
  2. customThe tan precipitate is collected
  3. washwashed with water
  4. customis dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-e2ef7bafd8bd423a9289c78c6c520a85
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Reaction notes

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