Methanol → tert-Butyl 4-(5-(3-fluorophenyl)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([N:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)=[C:10]3[CH:16]=[CH:15][N:14](S(C4C=CC=CC=4)(=O)=O)[C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C1COCC1.CO.[Li+].[OH-]>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([N:26]3[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]3)=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

tert-Butyl 4-(5-(3-fluorophenyl)-1-(phenyl sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.220 g, 0.410 mmol) was placed in 1:1 THF:MeOH (6 mL). 3M LiOH (0.683 mL, 2.05 mmol) was then added, and the reaction was stirred at 50° C. for 1 hour. The reaction was then cooled, added to water and extracted with DCM. The organic fractions were dried, filtered and concentrated to give the crude product tert-butyl 4-(5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.150 g, 92.29% yield), which was used without further purification.

Aufarbeitung

temperatureThe reaction was then cooled
extractionextracted with DCM
customThe organic fractions were dried
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-c2ad9115341940e8a9d885fe09601dba
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841304B2

Notizen zur Reaktion

Wird geladen…