Sodium Hydroxide → HCID 49779776, compound

HRID 1773256Notes

Reaction equation

[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.CS(O[CH2:21][C:22]([CH3:30])([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[CH3:23])(=O)=O.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([CH2:21][C:22]([CH3:30])([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH3:23])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (145 mg, 0.727 mmol), tetra n-butyl ammonium bromide (11 mg, 0.036 mmol), and 2-methyl-2-(pyridin-4-yl)propyl methanesulfonate (200 mg, 1.20 mmol) were taken into 50% NaOH (6 mL). The reaction mixture was heated overnight at 100° C. Reaction was monitored by TLC and LCMS. After completion of the reaction, the reaction mixture was extracted with EtOAc and water. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude compound was purified by column chromatography to yield 30 mg of product. 1H NMR (CDCl3, Freebase) d (ppm): 8.50 (d, 2H), 7.2-7.13 (m, 3H), 6.88 (d, 2H), 4.03 (s, 2H), 3.62 (s, 2H), 2.63 (t, 2H), 2.50 (s, 3H), 2.42 (s, 3H), 2.25 (t, 2H), 1.43 (s, 6H).

Workup

customReaction
customAfter completion of the reaction
extractionthe reaction mixture was extracted with EtOAc and water
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude compound was purified by column chromatography

Sources & evidence

ORD record: ord-00d1c9da2d014971840c9f6013cb63c8
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255094B2

Reaction notes

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