Lawesson's reagent → (S)-2'-bromo-4'-fluoro-7'-methoxyspiro[morpholine-3,9'-xanthene]-5-thione

HRID 455707Notes

Reaction equation

COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Br:23][C:24]1[CH:37]=[C:36]([F:38])[C:35]2[O:34][C:33]3[C:28](=[CH:29][C:30]([O:39][CH3:40])=[CH:31][CH:32]=3)[C@@:27]3([CH2:45][O:44][CH2:43][C:42](=O)[NH:41]3)[C:26]=2[CH:25]=1>C1(C)C=CC=CC=1>[Br:23][C:24]1[CH:37]=[C:36]([F:38])[C:35]2[O:34][C:33]3[C:28](=[CH:29][C:30]([O:39][CH3:40])=[CH:31][CH:32]=3)[C@@:27]3([CH2:45][O:44][CH2:43][C:42](=[S:10])[NH:41]3)[C:26]=2[CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

In a 250-mL flask, Lawesson's reagent (0.577 g, 1.427 mmol) and (S)-2′-bromo-4′-fluoro-7′-methoxyspiro[morpholine-3,9′-xanthen]-5-one (0.978 g, 2.481 mmol) were suspended in toluene (25 mL). An air-cooled condenser was attached, and the flask was heated in a 90° C. oil bath for 3 h. The mixture was then cooled and concentrated to give (S)-2′-bromo-4′-fluoro-7′-methoxyspiro[morpholine-3,9′-xanthene]-5-thione which was used in the next step without further purification.

Workup

customAn air-cooled condenser was attached
temperatureThe mixture was then cooled
concentrationconcentrated

Sources & evidence

ORD record: ord-b96bc4949a714493af58b3cc41cca129
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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