Trifluoroacetic acid → 1H-Pyrrolo[2,3-b]pyridine, 3-(cyclopropylmethyl)-1-(phenylsulfonyl)-
Reaktionsgleichung
[CH:1]1([CH:4]([C:6]2[C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:8]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:7]=2)O)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCCl>[CH:1]1([CH2:4][C:6]2[C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:8]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:7]=2)[CH2:2][CH2:3]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Cyclopropyl(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)methanol (0.285 g, 0.87 mmol) was dissolved in dry dichloromethane (9 mL) and chilled to 0° C. Triethylsilane (1.11 mL, 6.94 mmol, 8 eq.) and TFA (0.201 mL, 2.60 mmol, 3 eq.) were then added. The reaction mixture was stirred at 0° C. for 15 minutes and then allowed to warm to room temperature. After about 1.5 hours, the mixture was quenched with saturated sodium bicarbonate solution and extracted with DCM. The extracts were dried over sodium sulfate and concentrated. Flash 40 Biotage (40M cartridge, DCM to 5% EtOAc/DCM) afforded 3-(cyclopropylmethyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (159 mg, 59%). m/z (APCI-pos) M+1=313.1.
Aufarbeitung
- temperatureto warm to room temperature
- waitAfter about 1.5 hours
- customthe mixture was quenched with saturated sodium bicarbonate solution
- extractionextracted with DCM
- dry with materialThe extracts were dried over sodium sulfate
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-d165dda61d8b41b495d663d7e9e28f39
- Quelldatensatz
- uspto-grants-2012_12
- Patentnummer
- US08338452B2
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