Carbon Tetrachloride → HCID 86633187, compound

HRID 912054Notes

Reaction equation

[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[C:11](=[O:23])[N:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:3][CH:2]=1.C1C(=O)N([Br:32])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>>[Br:32][C:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[C:11](=[O:23])[N:12]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=[CH:14][CH:15]=2)=[O:9])=[C:3]([CH3:2])[CH:24]=1

Participants

Reactant 4

HCID 5943Carbon Tetrachloride

HCID 6547Azobisisobutyronitrile

HCID 67184N-bromobutanimide

HCID 57812316HCID 57812316, compound

Product 1

HCID 86633187HCID 86633187, compound

Conditions

Temperature: 80 °C

Procedure

The mixture of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid p-tolylamide (183 mg, 0.482 mmol), NBS (108 mg, 0.603 mmol) and 2,2′-Azo-bis-isobutyronitrile (8.08 mg, 0.0482 mmol) in carbon tetrachloride (5 ml, 50 mmol) was heated at 80° C. under an atmosphere of nitrogen for 24 h. After that time, the mixture was filtered to give the title compound as a beige solid that was used for further reaction without purification. MS (ES+): m/z 400.92/402.96 [MH+]. HPLC: tR=3.66 min (polar—5 min, ZQ3).

Workup

filtrationAfter that time, the mixture was filtered

Sources & evidence

ORD record: ord-8608a85fa90f4b6e870af7dac3dd52d1
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

Loading…