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

HRID 1765573Notes

Reaction equation

HRID 1765573 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-2235e55ef24542998f38b756b6a7ae32
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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