Piperidine → 5-Fluoro-4-(piperidin-1-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1696238Notes

Reaction equation

Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)CCC.CCOC(C)=O.C(=O)([O-])O.[Na+]>[F:8][C:7]1[C:2]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:3]2[CH:11]=[CH:10][NH:9][C:4]2=[N:5][CH:6]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (30 mg) and piperidine (50 mg) in 1-butanol (0.4 mL) was heated in the microwave reactor (120° C., 0.5 hour, 180° C., 2 hours). The reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc (10 mL) and half-saturated aqueous sodium hydrogencarbonate (10 mL). The aqueous phase was extracted with EtOAc (10 mL) two times and combined organic layers were washed with brine (20 mL), dried over MgSO4, and concentrated. Purification of the crude product by preparative silica gel thin-layer chromatography (EtOAc) gave 5-fluoro-4-(1-piperidinyl)-1H-pyrrolo[2,3-b]pyridine (10 mg) as a white solid.

Workup

temperatureto cool to ambient temperature
extractionThe aqueous phase was extracted with EtOAc (10 mL) two times
washwere washed with brine (20 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customPurification of the crude product by preparative silica gel thin-layer chromatography (EtOAc)

Sources & evidence

ORD record: ord-968c18d181db4cd5ad0b6d0b205c8976
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163767B2

Reaction notes

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