Cesium carbonate → HCID 68912769, compound

HRID 1986834Notes

Reaction equation

[F:1][C:2]1[C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=[C:4]([F:13])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:20][CH2:21][CH2:22][CH2:23]I>>[Cl:20][CH2:21][CH2:22][CH2:23][N:8]1[C:7]2[C:2]([F:1])=[CH:3][C:4]([F:13])=[CH:5][C:6]=2[O:11][CH2:10][C:9]1=[O:12]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 813631-Chloro-3-iodopropane

HCID 68914018865106-43-0

Product 1

HCID 68912769HCID 68912769, compoundYield 50%

Procedure

5,7-Difluoro-4H-benzo[1,4]oxazin-3-one (0.24 g, 1.3 mmol), Cs2CO3 (1.08 g, 3.3 mmol), and 1-chloro-3-iodopropane (0.296 g, 1.45 mmol) were mixed according to GP2. Purified by column chromatography (SiO2; heptanes/EtOAc, gradient 0 to 30% EtOAc) to give the title compound (0.17 g, 49%). Rf=0.66 (heptanes/EtOAc 1:1); 1H NMR (CDCl3) d 6.67-6.58 (m, 2H), 4.55 (s, 2H), 4.16-4.10 (m, 2H), 3.59-3.52 (m, 2H), 2.21-2.10 (m, 2H).

Workup

customPurified by column chromatography (SiO2; heptanes/EtOAc, gradient 0 to 30% EtOAc)

Sources & evidence

ORD record: ord-9de9da1fefc14172bb9399ef97408975
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550459B2

Reaction notes

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