Potassium Hydroxide → HCID 22477303, compound

HRID 1765571Notes

Reaction equation

HRID 1765571 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[C:8]([C:17]2[N:25](S(C3C=CC(C)=CC=3)(=O)=O)[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)=[CH:7]1)C.[OH-].[K+]>CO>[CH3:16][O:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:6]([CH2:5][C:4]([OH:36])=[O:3])[CH:7]=[C:8]2[C:17]1[NH:25][C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67158215HCID 67158215, compound

Product 1

HCID 22477303HCID 22477303, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of {5-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-indol-1-yl}-acetic acid ethyl ester [4.67 g, Reference Example 13(a)], methanol (250 mL) and aqueous potassium hydroxide (S5M, 25 mL) were heated under reflux for 7 hours. The methanol was removed under reduced pressure and the residue was treated with water (20 mL) and the pH of this solution was adjusted to 7 by addition of concentrated hydrochloric acid. The resulting yellow solid was filtered and subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and methanol (7:3, v/v) to give the title compound (1.69 g) as a white solid. MS: 320 (M−H+). HPLC (METHOD A): RT=6.67 minutes.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 7 hours
  3. customThe methanol was removed under reduced pressure
  4. additionthe residue was treated with water (20 mL)
  5. additionthe pH of this solution was adjusted to 7 by addition of concentrated hydrochloric acid
  6. filtrationThe resulting yellow solid was filtered
  7. additionsubjected to flash chromatography on silica eluting with a mixture of ethyl acetate and methanol (7:3

Sources & evidence

ORD record
ord-bba5e1baad884eb09131ba5dab7dc07a
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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