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

HRID 455658Notes

Reaction equation

[Br:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:17][CH3:18])=[CH:9][CH:10]=3)[C@@:5]3([CH2:23][O:22][CH2:21][C:20](=O)[NH:19]3)[C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:17][CH3:18])=[CH:9][CH:10]=3)[C@@:5]3([CH2:23][O:22][CH2:21][C:20](=[S:34])[NH:19]3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

In a 1-L flask, the (S)-2′-bromo-4′-fluoro-7′-methoxyspiro[morpholine-3,9′-xanthen]-5-one (3.16 g, 8.02 mmol) was suspended in toluene (75 mL). Lawesson's reagent (1.864 g, 4.61 mmol) was added. An air-cooled condenser was affixed, and the mixture was heated in a 90° C. oil bath for 2 h. The mixture was cooled and concentrated to afford crude (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 affixed
temperatureThe mixture was cooled
concentrationconcentrated

Sources & evidence

ORD record: ord-f5b7d08dc62f4d1086d8bc506159eaf5
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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