Tetrahydrofuran → (NE,R)-N-[1-(7-bromoquinolin-2-yl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 2285410Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12](=O)[CH3:13])=[N:9]2)=[CH:4][CH:3]=1.CC(C)C[S@:18]([NH2:20])=[O:19].[C:22](OCC)(=O)C.[CH2:28]1[CH2:32]OC[CH2:29]1>[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[C:12](=[N:20]/[S@@:18]([C:28]([CH3:29])([CH3:32])[CH3:22])=[O:19])/[CH3:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(7-bromo-quinolin-2-yl)-ethanone (1.42 g, 5.68 mmol) in THF (28 mL) was added titanium (IV) ethoxide (2.6 g, 2.35 mL, 11.4 mmol, tech. grade) followed by (R)-(+)-2-methyl-propanesulfinamide (825 mg, 6.82 mmol). The reaction mixture was stirred at 60° C. under nitrogen for 6 hours and allowed to cool. Brine was added followed by ethyl acetate and the suspension filtered through celite and the filter pad was washed with ethyl acetate. The ethyl acetate layer was separated, dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography using a gradient of iso-hexane/ethyl acetate 9:1 to 3:1 to give the title compound (448 mg, 22%) as an orange solid. 1H NMR (300 MHz, CDCl3) δ 1.38 (s, 9H), 2.99 (s, 3H), 7.71 (m, 2H), 8.16 (d, J=8.6 Hz, 1H), 8.24 (d, J=8.6 Hz, 1H), 8.37 (s, 1H). LCMS (m/z) 352.9/354.9 [M+H], Tr 3.14 minutes.

Workup

temperatureto cool
filtrationthe suspension filtered through celite
washthe filter pad was washed with ethyl acetate
customThe ethyl acetate layer was separated
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-2c70d134987641b3944cc0b71bbce3c3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145441B2

Reaction notes

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