Cesium carbonate → 6-Bromo-4-(3-chloropropyl)-8-fluoro-4H-benzo[1,4]oxazin-3-one

HRID 2103175Notes

Reaction equation

HRID 2103175 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:13])[C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:20][CH2:21][CH2:22][CH2:23]I>CCCCCCC.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:13])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:23][CH2:22][CH2:21][Cl:20])[C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 468564636-bromo-8-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 689111406-Bromo-4-(3-chloropropyl)-8-fluoro-4H-benzo[1,4]oxazin-3-oneYield 72.1%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

6-Bromo-8-fluoro-4H-benzo[1,4]oxazin-3-one (95MF44) (0.091 g, 0.37 mmol), Cs2CO3 (0.180 g, 0.55 mmol) and 3-chloro-1-iodopropane (0.083 g, 0.41 mmol) were mixed according to GP5. CC (SiO2; Heptane/EtOAc 9:1-4) gave the title compound (95MF50(2084)) (0.086 g, 72%). 1H NMR (CDCl3) δ 7.02-6.96 (m, 1H), 6.85 (d, J=5.2 Hz, 1H), 4.65 (s, 2H), 4.04-4.11 (m, 2H), 3.62 (t, J=6.2 Hz, 2H), 2.10-2.18 (m, 2H); 13C NMR (CDCl3) δ 163.8, 151.7 (d, J=250.9 Hz), 133.1 (d, J=14.6 Hz), 131.5 (d, J=3.8 Hz), 115.1 (d, J=21.5 Hz), 114.2 (d, J=10.0 Hz), 113.4 (d, J=3.4 Hz), 67.6, 42.2, 39.5, 30.0.

Sources & evidence

ORD record
ord-754d6714594c4a56b3a7382b2e148f23
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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