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

HRID 2285410
Notes
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Reaction equation

HRID 2285410 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 867060471-(7-Bromoquinolin-2-yl)ethanoneHCID 87277631(R)-(+)-2-methyl-propanesulfinamide

Product 1

HCID 89949697(NE,R)-N-[1-(7-bromoquinolin-2-yl)ethylidene]-2-methylpropane-2-sulfinamideYield 22%

Reagents, catalysts & solvents 2

HCID 76524
Titanium tetraethoxide
Catalyst
HCID 57417360Sodium chloride; waterSolvent

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

  1. temperatureto cool
  2. filtrationthe suspension filtered through celite
  3. washthe filter pad was washed with ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes