(Diethylamino)sulfur trifluoride → 5-(2-fluoro-2-(pyridin-4-yl)propyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1423284Notes

Reaction equation

[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6]([CH2:14][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)(O)[CH3:16])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.C(N(S(F)(F)[F:32])CC)C>C(Cl)Cl>[F:32][C:15]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)([CH3:16])[CH2:14][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:25][CH2:24][C:5]1=2

Participants

Conditions

Temperature: 2.5 °C

Procedure

1-(2,8-Dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol (150 mg) was dissolved in DCM (10 mL) and the solution was cooled to 0 to 5° C. Diethylaminosulfur trifluoride (0.15 mL) was added and the reaction mixture was allowed to warm to RT for 30 min. The reaction mixture was quenched with saturated aqueous sodium bicarbonate, the organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by HPLC.

Workup

temperatureto warm to RT for 30 min
customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
customthe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-63c0e2cf19a049b7aecad71cb668e6a7
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927571B2

Reaction notes

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