Sodium hydride → 2-(1-(4-cyano-3-ethoxyphenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

HRID 1254905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1254905
[H-].[Na+].C[O:4][C:5](=[O:17])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH3:16].[C:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][C:21]=1[O:30][CH2:31][CH3:32])#[N:19]>C1COCC1.C1COCC1.CN(C=O)C>[C:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[C:7]([CH2:6][C:5]([OH:4])=[O:17])=[C:8]2[CH3:16])(=[O:28])=[O:27])=[CH:22][C:21]=1[O:30][CH2:31][CH3:32])#[N:19]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 552808794-Cyano-3-ethoxybenzene-1-sulfonyl chlorideHCID 67218699methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

Produkt 1

HCID 452727612-(1-(4-cyano-3-ethoxyphenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred, ice-cooled (0° C.) suspension of sodium hydride (26.3 mg of a 60% dispersion in mineral oil, 0.686 mmol) in dry THF (10 ml) under an inert atmosphere of Argon is added dropwise (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester ((0.1 g, 0.49 mmol) in THF/DMF (4 ml of a 3:1 mixture). The reaction mixture is stirred at 0° C. for 1 hour and then treated with 4-cyano-3-ethoxy-benzenesulfonyl chloride (168 mg, 0.686 mmol) in dry THF (1 ml). Stirring continued at 0° C. for 10 minutes and at room temperature for 10 minutes and then the reaction mixture is poured onto water (50 ml). The mixture is extracted with ethyl acetate (2×50 ml) and the organic portions are combined, washed brine (50 ml), dried (MgSO4) and concentrated in vacuo. The resulting crude is purified by chromatography on silica eluting with iso-hexane/ethyl acetate (0%-20% ethyl acetate) to yield the titled product. (MH+ 414).

Aufarbeitung

  1. temperatureTo a stirred, ice-cooled
  2. stirringStirring
  3. waitcontinued at 0° C. for 10 minutes and at room temperature for 10 minutes
  4. additionthe reaction mixture is poured onto water (50 ml)
  5. extractionThe mixture is extracted with ethyl acetate (2×50 ml)
  6. washwashed brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe resulting crude is purified by chromatography on silica eluting with iso-hexane/ethyl acetate (0%-20% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c95a7c7eda1240aaa9eddcf48b71cca0
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455645B2

Notizen zur Reaktion

Wird geladen…