Sodium Methoxide → methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 269487Notes

Reaction equation

HRID 269487 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][N:11](S(C3C=CC(C)=CC=3)(=O)=O)[C:8]2=[N:9][CH:10]=1)=[O:4].C[O-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 497589101H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, methyl ester

Product 1

HCID 22832049methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
65 °C

Procedure

A suspension of 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (5.4 g, 16 mmol) in MeOH (100 mL) with NaOMe in MeOH (20 mL, 25% wt., excess) was heated at 65° C. for 1 hour. The resulting material was concentrated from MeOH, diluted with H2O (100 mL), and pH adjusted to 6 with 1N HCl. The aqueous solution was partitioned with EtOAc (100 mL) and the organic extraction was dried over Na2SO4 and dried in vacuo. The residue was purified with flash chromatography over silica gel in an elution from 99:1 CH2Cl2:MeOH to 92:8 CH2Cl2:MeOH. Yield 1.8 g, beige powder.

Workup

  1. concentrationThe resulting material was concentrated from MeOH
  2. additiondiluted with H2O (100 mL)
  3. customThe aqueous solution was partitioned with EtOAc (100 mL)
  4. extractionthe organic extraction
  5. dry with materialwas dried over Na2SO4
  6. customdried in vacuo
  7. customThe residue was purified with flash chromatography over silica gel in an elution from 99:1 CH2Cl2

Sources & evidence

ORD record
ord-59a2f3afe7ea4e7fbe027a78e15530c6
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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