2,2'-Bipyridine → HCID 71138340, compound

HRID 1503602Notes

Reaction equation

C[Si](C)(C)[O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:8][CH:7]=1)=[CH2:5].Br[CH:20]([C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=1)[C:21]([F:24])([F:23])[F:22].N1C=CC=CC=1C1C=CC=CN=1>ClC1C=CC=CC=1Cl.Cl[Cu]>[N:12]1([C:9]2[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH2:3][CH:20]([C:25]3[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=3)[C:21]([F:24])([F:23])[F:22])=[CH:7][CH:8]=2)[CH:16]=[N:15][CH:14]=[N:13]1

Participants

Conditions

Temperature: 180 °C

Procedure

To a stirred solution of 1-(4-(1-(trimethylsilyloxy)vinyl)phenyl)-1H-1,2,4-triazole (6 g, 23 mmol) and 1-(1-bromo-2,2,2-trifluoro-ethyl)-3,5-dichlorobenzene (7.1 g, 34.7 mmol) in 1,2-dichlorobenzene (30 mL) was degassed with argon. To this CuCl (0.23 g, 2.31 mmol) and 2,2-bipyridyl (0.73 g, 4.63 mmol) was added to the above reaction mixture and the resultant reaction mixture was heated to 180° C. for 18 h. After completion of the reaction (by TLC), the reaction mixture was absorbed onto silica gel and purified by column chromatography (SiO2; 10% EtOAc in petroleum ether) to afford title compound as a solid (3 g, 31%): 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 8.15 (s, 1H), 8.10 (d, J=8.3 Hz, 2H), 7.82 (d, J=8.3 Hz, 2H), 7.33 (m, 1H), 7.30 (m, 2H), 4.20 (m, 1H), 3.63 (m, 2H); ESIMS m/z 412.14 ([M−H]−).

Workup

customthe resultant reaction mixture
customAfter completion of the reaction (by TLC)
customthe reaction mixture was absorbed onto silica gel
custompurified by column chromatography (SiO2; 10% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-aa7fcbeb42ce47f1bdd0fe292bef69c7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212163B2

Reaction notes

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