Carbazole → HCID 86702142, compound

HRID 1776211Notes

Reaction equation

[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:17]([CH3:21])([CH3:20])[C:18]#[CH:19]>CN(C)C=O>[CH3:20][C:17]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)([C:18]#[CH:19])[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of carbazole (2.500 g, 15.0 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0° C. was added 60% sodium hydride in mineral oil (0.718 g, 17.9 mmol) and the mixture was stirred at 0° C. for 1 hr. 3-Chloro-3-methyl-1-butyne (2.300 g, 22.4 mmol) was added and the reaction mixture was stirred at 0° C. for 1 hr and then slowly warmed to room temperature and stirred for 16 hrs. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (10-70% methylene chloride/hexanes) to afford the desired product as a light brown solid (1.7 g, 49%). 1H NMR (300 MHz, CDCl3) δ 8.10 (d, 2H, J=7.5 Hz), 8.04 (d, 2H, J=8.7 Hz), 7.41 (td, 2H, J=8.1, 1.5 Hz), 7.24 (t, 2H, J=7.5 Hz), 2.67 (s, 1H), 2.28 (s, 6H).

Workup

stirringthe reaction mixture was stirred at 0° C. for 1 hr
temperatureslowly warmed to room temperature
stirringstirred for 16 hrs
customThe mixture was partitioned between water and ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried (anhydrous sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (10-70% methylene chloride/hexanes)

Sources & evidence

ORD record: ord-2f316381517b4febac6a8285a3c415c4
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265772B2

Reaction notes

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