(2-Chloro-6-hydroxyphenyl)boronic acid → (S)-Methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-chloro-6'-hydroxy-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
Reaction equation
[CH2:1]([O:4][C:5]1([CH3:38])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22](Br)[CH:21]=4)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:27])[C:12]=2[C@H:28]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:29]([O:31][CH3:32])=[O:30])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[Cl:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([OH:46])[C:41]=1B(O)O>>[CH2:1]([O:4][C:5]1([CH3:38])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:21]=[C:22]([C:41]5[C:42]([OH:46])=[CH:43][CH:44]=[CH:45][C:40]=5[Cl:39])[CH:23]=[CH:24][CH:25]=4)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:27])[C:12]=2[C@H:28]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:29]([O:31][CH3:32])=[O:30])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]Participants
3
Reactant 2
Product 1
Procedure
Prepared from (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate and (2-chloro-6-hydroxyphenyl)boronic acid using the same procedure as intermediate 168 in 81% yield. 1H NMR (400 MHz, CDCl3) [note: 4H of piperidine and phenolic —OH not observed] δ 8.13-8.06 (m, 1H), 7.97 (s, 1H), 7.62 (t, J=7.8 Hz, 1H), 7.38 (d, J=7.5 Hz, 1H), 7.26-7.20 (m, 1H), 7.11 (d, J=8.0 Hz, 1H), 6.97 (d, J=8.3 Hz, 1H), 6.89-6.77 (m, 1H), 6.06-5.90 (m, 1H), 5.39 (dd, J=17.1, 1.5 Hz, 1H), 5.29-5.20 (m, 1H), 5.15-5.04 (m, 1H), 3.99 (d, J=4.8 Hz, 2H), 3.76 (s, 3H), 2.63 (br. s., 3H), 2.07-1.91 (m, 3H), 1.79-1.65 (m, 1H), 1.35 (s, 3H), 1.25 (s, 9H). LCMS (M+1)=633.3.
Sources & evidence
- ORD record
- ord-edb06dd2907342bfb62f993ea0e4f9cf
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906929B2
Reaction notes
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