Potassium Hydroxide → 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 549014Notes

Reaction equation

HRID 549014 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:21](S(C2C=CC(C)=CC=2)(=O)=O)[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=1.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[NH:21][C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 224774382-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 224772272-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridineYield 80.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [1.45 g, Reference Example 13(b)] in methanol (100 mL) was treated with potassium hydroxide (5N, 15 mL) then heated at reflux for 2 hours. The reaction mixture was cooled then evaporated. The residue was treated with water (150 mL) and the resulting solid was filtered then dried to give the title compound (0.75 g) as a tan solid, m.p. 226-227° C. MS: 278 (MH+).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. customthen evaporated
  5. additionThe residue was treated with water (150 mL)
  6. filtrationthe resulting solid was filtered
  7. customthen dried

Sources & evidence

ORD record
ord-f9fb8d20b51e4cf3bde8f3f8153465f7
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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