Cesium carbonate → 4-(3-chloropropyl)-5,6-difluoro-4H-benzo[1,4]oxazin-3-one

HRID 1986838Notes

Reaction equation

HRID 1986838 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]=[CH:4][C:3]=1[F:13].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])=[C:3]([F:13])[CH:4]=[CH:5][C:6]=2[O:11][CH2:10][C:9]1=[O:12]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 689101445,6-Difluoro-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 689103024-(3-chloropropyl)-5,6-difluoro-4H-benzo[1,4]oxazin-3-oneYield 75%

Procedure

5,6-Difluoro-4H-benzo[1,4]oxazin-3-one (0.13 g, 0.69 mmol), Cs2CO3 (0.45 g, 1.4 mmol), and 1-chloro-3-iodopropane (0.15 g, 0.76 mmol) were mixed according to GP2. Purified by column chromatography (SiO2; heptanes/EtOAc, gradient 0 to 30% EtOAc) to give the title compound (0.13 g, 75%). Rf=0.60 (heptanes/EtOAc 1:1); 1H NMR (CDCl3) d 6.88-6.74 (m, 2H), 4.52 (s, 2H), 4.19-4.14 (m, 2H), 3.58 (t, J=6.4 Hz, 2H), 2.22-2.14 (m, 2H); 13C NMR (CDCl3) d 165.1, 147.5 (dd, J=242.5 Hz, J=12.7 Hz), 143.8 (t, J=3.0 Hz), 140.7 (dd, J=249.8 Hz, J=17.3 Hz), 119.8 (d, J=4.6 Hz), 111.9 (dd, J=7.4 Hz, J=3.9 Hz), 111.2 (d, J=18.8 Hz), 68.4, 42.4 (d, J=9.7 Hz), 42.1, 31.1 (d, J=3.5 Hz).

Workup

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

Sources & evidence

ORD record
ord-475b482ac1d641778bfffde12aa2680a
Source dataset
uspto-grants-2009_06
Patent number
US07550459B2

Reaction notes

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