Sodium Hydroxide → HCID 49779777, compound

HRID 1773257Notes

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]1([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:24][CH2:23]1)(=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]3([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[CH2:24][CH2:23]3)[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 (183 mg, 0.917 mmol), tetra n-butyl ammonium bromide (14 mg, 0.045 mmol), and (1-(pyridin-4-yl)cyclopropyl)methyl methanesulfonate (250 mg, 1.10 mmol) were taken into 50% NaOH (6 mL). The reaction mixture was stirred overnight at 100° C. Reaction was monitored by TLC and LCMS. After completion of the reaction, 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 37 mg of product. 1H NMR (CDCl3, Freebase) d (ppm): 8.45 (d, 2H), 7.1-7.0 (m, 3H), 6.9 (d, 2H), 4.28 (s, 2H), 3.63 (s, 2H), 2.7 (t, 2H), 2.5-2.6 (m, 5H), 2.42 (s, 3H), 1.0-0.85 (m, 4H).

Workup

customReaction
customAfter completion of the reaction, reaction mixture
extractionwas 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-d47ba945bed14b0da0b430468e2bd4b0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255094B2

Reaction notes

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