2-(Trifluoromethyl)pyridine-5-boronic Acid → N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[6-(trifluoromethyl)-3-pyridinyl]-1H-indazole-4-carboxamide
Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[F:27][C:28]([F:39])([F:38])[C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=[C:2]([C:32]2[CH:33]=[N:34][C:29]([C:28]([F:39])([F:38])[F:27])=[CH:30][CH:31]=2)[CH:3]=1)=[O:15]Komponenten
3
Edukt 2
Produkt 1
Versuchsvorschrift
The title compound was prepared in a similar manner as described for example 8 from 6-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide (110 mg, 0.264 mmol) and [6-(trifluoromethyl)-3-pyridinyl]boronic acid (75 mg, 0.395 mmol). The product was collected as a solid (75 mg, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1H) 9.30 (d, J=2.02 Hz, 1H) 8.66 (t, J=4.93 Hz, 1H) 8.58 (dd, J=8.08, 2.02 Hz, 1H) 8.45 (s, 1H) 8.38 (s, 1H) 8.07 (d, J=8.34 Hz, 1H) 7.98-8.01 (m, 1H) 5.90 (s, 1H) 5.20 (dt, J=13.14, 6.57 Hz, 1H) 4.41 (br. s., 1H) 4.40 (br. s., 1H) 2.22 (s, 3H) 2.13 (s, 3H) 1.53 (s, 3H) 1.51 (s, 3H). LC-MS (ES) m/z=484.1 [M+H]+
Aufarbeitung
- customThe product was collected as a solid (75 mg, 57%)
Quellen und Nachweise
- ORD-Eintrag
- ord-833abb872e694ee6a4c81bc9fd31d76a
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08846935B2
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