HCID 86612139, compound → HCID 67147621, compound

HRID 490468Notes

Reaction equation

HRID 490468 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]([O:16]C)=[O:15])[N:8]([CH3:18])[CH:7]=[C:6]2[C:19]1[N:27]([S:28]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH:20]=1>[OH-].[K+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]([OH:16])=[O:15])[N:8]([CH3:18])[CH:7]=[C:6]2[C:19]1[N:27]([S:28]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=2)(=[O:29])=[O:30])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH:20]=1

Participants

3

Reactant 1

HCID 86612139HCID 86612139, compound

Product 1

HCID 67147621HCID 67147621, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of methyl {5-methoxy-1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-yloxy}acetate, (0.91 g; 1.751 mmol) in methanolic potassium hydroxide (74 ml at 1 g/ml) is placed in a 100 ml round-bottomed flask, at 20° C. for 16 hours with agitation. After reaction, the precipitate formed is filtered off, and rinsed with methanol (20 ml). A suspension of the above solid in water (30 ml) is placed in a 250 ml Erlenmeyer flask and the pH is then adjusted to 4 with 2N aqueous hydrochloric acid. The yellow solid formed is triturated in the reaction mixture and is then filtered, rinsed with water and dried under reduced pressure. {5-Methoxy-1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-yloxy}acetic acid (0.666 g; 98%) is isolated, the characteristics of which are as follows:

Workup

  1. customAfter reaction
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washrinsed with methanol (20 ml)
  5. additionA suspension of the above solid in water (30 ml)
  6. customThe yellow solid formed
  7. customis triturated in the reaction mixture
  8. filtrationis then filtered
  9. washrinsed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-1b29787747cb4d448b21bfbaf51e4e80
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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