Potassium Hydroxide → 2-(5-Methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

HRID 549027Notes

Reaction equation

HRID 549027 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:28](S(C2C=CC(C)=CC=2)(=O)=O)[C:16]2[N:17]=[CH:18][CH:19]=[C:20]([C:21]([O:23]C(C)(C)C)=[O:22])[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:28][C:16]2[N:17]=[CH:18][CH:19]=[C:20]([C:21]([OH:23])=[O:22])[C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86601932HCID 86601932, compound

Product 1

HCID 224772042-(5-Methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acidYield 51.5%

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-4 carboxylic acid, tert-butyl ester [106 mg, Reference Example 2(n)] in methanol (10 mL) was treated with potassium hydroxide solution (1 mL, 5N) then heated at reflux temperature for 1 hour and then evaporated. The residue was treated with water (15 mL) and the mixture washed with ethyl acetate (10 mL). The pH of the aqueous solution was then adjusted to 4 by addition of hydrochloric acid and cooled in ice. The resulting yellow solid was filtered washed well with water and then dried at 80° C. under vacuum to give the title compound (33 mg) as a yellow solid, m.p.>300° C. MS: 322 (MH+).

Workup

  1. temperaturethen heated
  2. temperatureat reflux temperature for 1 hour
  3. customevaporated
  4. additionThe residue was treated with water (15 mL)
  5. washthe mixture washed with ethyl acetate (10 mL)
  6. additionThe pH of the aqueous solution was then adjusted to 4 by addition of hydrochloric acid
  7. temperaturecooled in ice
  8. filtrationThe resulting yellow solid was filtered
  9. washwashed well with water
  10. customdried at 80° C. under vacuum

Sources & evidence

ORD record
ord-b9d9a47f5726464c814cb88f0d4dcc6d
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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