Sodium Iodide → HCID 10172464, compound

HRID 2102565Notes

Reaction equation

HRID 2102565 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][C:13]([F:16])=[C:14]([F:15])[C:9]=2[O:8][CH2:7][C:6]1=[O:17].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:26]([CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH2:27][CH2:28][CH3:29]>CCCCCCC.CCOC(C)=O>[CH2:26]([CH:30]1[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][CH2:4][N:5]2[C:10]3[CH:11]=[CH:12][C:13]([F:16])=[C:14]([F:15])[C:9]=3[O:8][CH2:7][C:6]2=[O:17])[CH2:32][CH2:31]1)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 68911066HCID 68911066, compound

Product 1

HCID 10172464HCID 10172464, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

4-(3-Chloropropyl)-7,8-difluoro-4H-benzo[1,4]oxazin-3-one (81MF2082b) (0.16 g, 0.60 mmol), K2CO3 (0.17 g, 11.9 mmol), NaI (0.18 g, 11.9 mmol) and 4-butylpiperidine (0.09 g, 0.63 mmol) were mixed according to GP12. CC (SiO2; Heptane/EtOAc 10:1-4) gave the title compound (81MF2082x) (0.14 g, 65%). 1H NMR (CDCl3) δ 6.88-6.76 (m, 2H) 4.66 (s, 2H), 3.96 (t, J=7.2 Hz, 2H), 2.84 (d, J=11.2, 2H), 2.34 (t, J=6.8 Hz, 2H), 1.91-1.78 (m, 4H), 1.67 (d J=9.6 Hz, 2H), 1.30-1.15 (m, 9H); 13C NMR (CDCl3) δ 163.1, 147.4 (q, J=245.0 Hz, J=10.6 Hz), 140.1 (q, J=248.7 Hz, J=15.7 Hz), 135.4 (d, J=12.0 Hz), 126.5, 109.5 (d, J=18.4 Hz), 109.0 (q, J=7.6 Hz, J=3.8 Hz), 67.8, 55.8, 52.3, 40.1, 36.4, 35.9, 32.7, 29.1, 24.8, 23.0, 14.2.

Sources & evidence

ORD record
ord-2d26947d701b4477a5124f35d921094f
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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