Potassium Hydroxide → HCID 67061262, compound

HRID 729792Notes

Reaction equation

HRID 729792 reaction equation
[C:1]([O:5][C:6](=[O:40])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[CH:20][N:19](S(C4C=CC(C)=CC=4)(=O)=O)[C:16]3=[N:17][CH:18]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CO.CC(C)=O.[OH-].[K+]>C(O)(=O)C>[C:1]([O:5][C:6](=[O:40])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21894497Aceton-methanolHCID 67061204HCID 67061204, compound

Product 1

HCID 67061262HCID 67061262, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]-benzoic acid tert-butyl ester (1.07 g, 1.82 mmol) in a 1:1 MeOH/acetone solution (40 mL total) was added 4 mL of a 50% KOH (aq) solution. The reaction mixture was stirred for 20 hours at ambient temperature. Glacial acetic acid was added dropwise until the solution had a pH=6. The product was extracted into ethyl acetate and dried over Na2SO4. The material was adsorbed onto silica gel and purified by flash chromatography in an ethyl acetate and hexane gradient, affording 3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid tert-butyl ester as a colorless oil that started to crystallize into a white solid (1.97 g, quantitative yield). 1H NMR (500 MHz, CDCl3) δ 11.34 (s, 1H), 8.50 (s, 2H), 8.21 (s, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.75 (m, 2H), 7.55 (m, 2H), 7.40 (t, J=6.0 Hz, 1H), 7.10 (m, 2H), 3.88 (s, 3H), 1.25 (s, 9H). MS: m/e 401.1 (M+H+).

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. dry with materialdried over Na2SO4
  3. custompurified by flash chromatography in an ethyl acetate and hexane gradient

Sources & evidence

ORD record
ord-83e99ab60aff44ddbf662aa47fdc0210
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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