Reaction equation
Br[C:2]1[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].O1CCCCC1[N:33]1[C:37](B2OC(C)(C)C(C)(C)O2)=[CH:36][CH:35]=[N:34]1>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:21]=[C:2]([C:35]3[NH:34][N:33]=[CH:37][CH:36]=3)[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[N:4][CH:5]=2)=[CH:11][CH:12]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in an analogous fashion to that described in Example 26 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((2-hydroxyethyl)(methyl)amino)nicotinamide (Stage 23.1) and 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to afford a yellow resin. UPLC-MS (Condition 3) tR=0.97 min, m/z=438.1 [M+H]+, m/z=436.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.77 (s, 3H) 3.37-3.49 (m, 2H) 3.49-3.65 (m, 2H) 4.62 (br. s, 1H) 6.47 (d, J=1.96 Hz, 1H) 7.33 (d, J=9.05 Hz, 2H) 7.72-7.85 (m, 1H) 7.85-7.96 (m, 2H) 8.14 (br. s, 1H) 8.71 (d, J=1.96 Hz, 1H) 10.26 (s, 1H) 12.58-13.18 (m, 1H).
Workup
- customto afford a yellow resin
Sources & evidence
- ORD record
- ord-08b647d6323941b8ab916a24df7b4fd4
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340537B2
Linked notes
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