2,2'-Bipyridine → HCID 67109927, compound

HRID 455321Notes

Reaction equation

Br[C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][CH3:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[F:18][C:19]1[CH:33]=[CH:32][C:22]([CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:21]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][S:39](=[O:43])(=[O:42])[NH:40][CH3:41])[CH:20]=1.N1C=CC=CC=1C1C=CC=CN=1>CN1C(=O)CCC1.ClCCl.[Cu-]=O>[C:27]([O:26][C:25]([NH:24][CH2:23][C:22]1[CH:32]=[CH:33][C:19]([F:18])=[CH:20][C:21]=1[O:34][CH2:35][CH2:36][CH2:37][CH2:38][S:39]([N:40]([C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][CH3:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)[CH3:41])(=[O:43])=[O:42])=[O:31])([CH3:30])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl 5-bromo-8-methoxy-1,6-naphthyridine-7-carboxylate (2.4 mmol), tert-butyl 4-fluoro-2-(4-(N-methylsulfamoyl)butoxy)benzylcarbamate (Example 19; 2.6 mmol), 2,2′-bipyridine (3.1 mmol) and copper (I) oxide (3.1 mmol) in NMP (30 ml) was stirred at 120° C. under nitrogen atmosphere for 10 hours. The reaction mixture was diluted with dichloromethane and filtered off. The filtrate was washed with 10% 2-[2-(bis(carboxylatomethyl)amino)ethyl-(carboxylatomethyl)amino]acetate (EDTA) disodium salt solution, saturated NaHCO3 solution and brine.

Workup

filtrationfiltered off
washThe filtrate was washed with 10% 2-[2-(bis(carboxylatomethyl)amino)ethyl-(carboxylatomethyl)amino]acetate (EDTA) disodium salt solution, saturated NaHCO3 solution and brine

Sources & evidence

ORD record: ord-f6f4847779a145deb6a9cadafe35bd02
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497270B2

Reaction notes

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