4'-Fluoro-3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile → 4'-Fluoro-3'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrile

HRID 1180246Notes

Reaction equation

HRID 1180246 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([C:29]#[N:30])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1>>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:24]([C:29]#[N:30])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:21][C:22]=1[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 224735984'-Fluoro-3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrileHCID 674869102-(3-Bromo-8-fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 179648364'-Fluoro-3'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrileYield 56%

Procedure

2-(3-Bromo-8-fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 4′-fluoro-3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile (prepared as described in WO 02/074773) as described in Example 1 to give 4′-fluoro-3′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-2-carbonitrile as an off-white solid (217 mg, 56%): δH (360 MHz, CDCl3) 1.74 (6H, s), 2.15 (1H, s), 7.22 (1H, t, J 7), 7.40 (1H, t, J 9), 7.48-7.73 (5H, m), 7.79-7.81 (2H, m), 8.06 (1H, dd, J 7 and 2); m/z (ES+) 390 [MH+].

Sources & evidence

ORD record
ord-2634695b13b744eb95820b5229039604
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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