2-Bromo-4-fluorobenzonitrile → 4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
Reaction equation
Br[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[C:12]1[N:17]=[C:16]([C:18]2[N:22]3[CH:23]=[CH:24][C:25]([C:27]([CH3:37])([O:29][Si:30]([CH2:35][CH3:36])([CH2:33][CH3:34])[CH2:31][CH3:32])[CH3:28])=[N:26][C:21]3=[N:20][CH:19]=2)[CH:15]=[CH:14][CH:13]=1.[F:38][C:39]1[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41]([B:47]2[O:51][C:50]([CH3:53])([CH3:52])[C:49]([CH3:55])([CH3:54])[O:48]2)[CH:40]=1>>[F:38][C:39]1[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41]([B:47]2[O:51][C:50]([CH3:53])([CH3:52])[C:49]([CH3:55])([CH3:54])[O:48]2)[CH:40]=1.[F:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([C:18]3[N:22]4[CH:23]=[CH:24][C:25]([C:27]([CH3:28])([O:29][Si:30]([CH2:31][CH3:32])([CH2:35][CH3:36])[CH2:33][CH3:34])[CH3:37])=[N:26][C:21]4=[N:20][CH:19]=3)[N:17]=2)[CH:9]=1Participants
5
Reactant 3
Product 2
Procedure
4-Fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl }benzonitrile was synthesised from 2-bromo-4-fluorobenzonitrile following the procedure in Example 22. 3-(6-Bromopyridin-2-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine was coupled to 4-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl }benzonitrile following the procedure in Example 2 to give 4-fluoro-2-{6-[7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidin-3-yl]pyridin-2-yl }benzonitrile as an orange oil.
Sources & evidence
- ORD record
- ord-458236b92d7e4f99b4ebcc6065a8f07f
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030128B2
Reaction notes
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