tert-Butyl (1-(4-((6-chloro-3-nitropyridin-2-yl)amino)phenyl)cyclobutyl)carbamate → Tert-butyl (1-{4-[(6-{3-[4-(dimethylcarbamoyl)piperidin-1-yl]phenyl}-3-nitropyridin-2-yl)amino]phenyl}cyclobutyl)carbamate

HRID 1852914Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[C:5]([N+:27]([O-:29])=[O:28])=[CH:4][CH:3]=1.[CH3:30][N:31]([CH3:55])[C:32]([CH:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42](B3OC(C)(C)C(C)(C)O3)[CH:41]=2)[CH2:36][CH2:35]1)=[O:33]>C1(C)C=CC=CC=1.CCO>[CH3:30][N:31]([CH3:55])[C:32]([CH:34]1[CH2:35][CH2:36][N:37]([C:40]2[CH:41]=[C:42]([C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:14]=[CH:13][C:12]([C:15]5([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:18][CH2:17][CH2:16]5)=[CH:11][CH:10]=4)[C:5]([N+:27]([O-:29])=[O:28])=[CH:4][CH:3]=3)[CH:43]=[CH:44][CH:45]=2)[CH2:38][CH2:39]1)=[O:33]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl (1-{4-[(6-chloro-3-nitropyridin-2-yl)amino]phenyl}cyclobutyl)carbamate (4.1 g, 9.8 mmol) in toluene/EtOH/saturated NaHCO3 (200/200/20 mL), were added N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperidine-4-carboxamide. (4.2 g, 12 mmol), Pd(PPh4)3 (563 mg, 0.49 mmol). The mixture was heated at 100° C. for 18 h. The mixture was filtered through celite, separated and evaporated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate/methanol, 85:15:1.5) to give the titled compound as a pale red solid (5.4 g, 91%)

Workup

filtrationThe mixture was filtered through celite
customseparated
customevaporated
customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate/methanol, 85:15:1.5)

Sources & evidence

ORD record: ord-6f4bfa45abbf4d4cbac568e116a36309
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962619B2

Reaction notes

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