2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → 3'-[7-(1-Hydroxy-1-methylethyl)imidazo[1,2-alpha]pyrimidin-3-yl]-4,2',6'-trifluorobiphenyl-2-carbonitrile
Reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:23]2[C:24]([F:39])=[C:25]([C:30]3[C:31]([C:37]#[N:38])=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[C:26]([F:29])=[CH:27][CH:28]=2)O1>>[OH:14][C:11]([C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:27]3[C:26]([F:29])=[C:25]([C:30]4[C:31]([C:37]#[N:38])=[CH:32][C:33]([F:36])=[CH:34][CH:35]=4)[C:24]([F:39])=[CH:23][CH:28]=3)=[CH:3][N:4]=[C:5]2[N:10]=1)([CH3:13])[CH3:12]Participants
3
Reactant 2
Product 1
Procedure
2-(3-Bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol was coupled with 3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-4,2′,6′-trifluorobiphenyl-2-carbonitrile as described in Example 65 to give 3′-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]-4,2′,6′-trifluorobiphenyl-2-carbonitrile as an off-white solid: δH (400 MHz, d6-DMSO) 1.51 (6H, s), 7.42 (1H, d, J 7), 7.54-7.58 (1H, m), 7.80-7.85 (1H, m), 7.89-7.96 (3H, m), 8.14 (1H, dd, J 9 and 2), 8.78 (1H, dd, J 7 and 3).
Sources & evidence
- ORD record
- ord-299f9082c053431f9991dcdd334333fd
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900215B2
Reaction notes
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