Potassium Hydroxide → HCID 22477526, compound

HRID 549012Notes

Reaction equation

HRID 549012 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH:11]=[C:10]2[C:17]1[N:25](S(C2C=CC(C)=CC=2)(=O)=O)[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)C.[OH-].[K+]>CO>[CH3:16][N:12]1[C:13]2[C:9](=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:36])=[O:3])=[CH:15][CH:14]=2)[C:10]([C:17]2[NH:25][C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)=[CH:11]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67157837HCID 67157837, compound

Product 1

HCID 22477526HCID 22477526, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-yloxy}-acetic acid ethyl ester [500 mg, Reference Example 15(b)] in methanol (25 mL) was treated with potassium hydroxide (5N, 3 mL) and then heated at reflux for 16 hours. The solvent was removed under reduced pressure and the residue was treated with water (10 mL). The pH of this mixture was adjusted to 7 by addition of acetic acid and the resulting colourless solid was collected by filtration then dried to give the title compound (170 mg) as a colourless solid, m.p.>300° C. MS: 322 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue was treated with water (10 mL)
  5. additionThe pH of this mixture was adjusted to 7 by addition of acetic acid
  6. filtrationthe resulting colourless solid was collected by filtration
  7. customthen dried

Sources & evidence

ORD record
ord-83ad6636d4364e0a999160117b8dc544
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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