Cyclohexylamine → N-cyclohexyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 1696237Notes

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.[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CN1C(=O)N(C)CC1.CCOC(C)=O.C(=O)([O-])O.[Na+]>[CH:12]1([NH:18][C:2]2[C:3]3[CH:11]=[CH:10][NH:9][C:4]=3[N:5]=[CH:6][C:7]=2[F:8])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (30 mg) and cyclohexylamine (87 mg) in DMI (0.4 mL) was heated in the microwave reactor (200° C., 4 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 (2×10 mL) 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 N-cyclohexyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-amine (5 mg) as a yellow solid.

Workup

temperatureto cool to ambient temperature
extractionThe aqueous phase was extracted with EtOAc (2×10 mL)
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-d327a34e7126459aacec2eb968ca08f8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163767B2

Reaction notes

Loading…