2-Fluoro-6-hydroxyphenylboronic acid → (S)-Methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-fluoro-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].[F: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[F: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-fluoro-6-hydroxyphenyl)boronic acid using the same procedure as intermediate 168 in 75% yield. 1H NMR (400 MHz, CDCl3) δ 8.19-7.99 (m, 2H), 7.61 (t, J=7.8 Hz, 1H), 7.46 (br. s., 1H), 7.25 (d, J=6.5 Hz, 1H), 6.92-6.74 (m, 3H), 6.13-5.78 (m, 2H), 5.59-5.47 (m, 1H), 5.39 (dd, J=17.2, 1.6 Hz, 1H), 5.20-4.99 (m, 1H), 4.00 (d, J=4.8 Hz, 2H), 3.76 (s, 3H), 2.72-2.54 (m, 3H), 2.05-1.87 (m, 3H), 1.79-1.64 (m, 1H), 1.35 (s, 3H), 1.25 (s, 9H). LCMS (M+1)=617.35.
Sources & evidence
- ORD record
- ord-ca6aa4c459c942c7a282ac1c66a5beb1
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906929B2
Reaction notes
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