Water → 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one

HRID 931549Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[N:13]=[C:12]([F:17])[C:11]=2[OH:18])=[O:9])[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:18][C:11]1[C:12]([F:17])=[N:13][C:14]([Cl:16])=[CH:15][C:10]=1[C:8]2=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of (5-bromo-2-fluorophenyl)(6-chloro-2-fluoro-3-hydroxypyridin-4-yl)methanone (730 g, 2.10 mol) in dioxane (6 L) was treated with Cs2CO3 (1024 g, 3.14 mol). The reaction mixture was heated to 100° C. for 5 hours and then cooled to RT. Water (9 L) was added and the mixture was stirred vigorously. The resulting solids were filtered, washed with water (1 L×2), hexanes (1 L×1), and EtOAc (700 mL) to provide 602 g of 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one as a light yellow solid.

Workup

temperaturecooled to RT
filtrationThe resulting solids were filtered
washwashed with water (1 L×2), hexanes (1 L×1), and EtOAc (700 mL)

Sources & evidence

ORD record: ord-0f75fa23963345d9bbd7117834960838
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296759B2

Reaction notes

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