(2'-Cyano-2-fluoro-[1,1'-biphenyl]-3-yl)boronic acid → 2'-Fluoro-3'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrile

HRID 1180250Notes

Reaction equation

HRID 1180250 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.[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[C:25]=1[F:33])#[N:17]>>[F:33][C:25]1[C:26]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]3=[N:4][CH:3]=2)=[CH:27][CH:28]=[CH:29][C:24]=1[C:19]1[C:18]([C:16]#[N:17])=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 11644397(2'-Cyano-2-fluoro-[1,1'-biphenyl]-3-yl)boronic acidHCID 674869102-(3-Bromo-8-fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 103856572'-Fluoro-3'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrileYield 30%

Procedure

2-(3-Bromo-8-fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 2′-cyano-2-fluorobiphenyl-3-boronic acid (prepared as described in WO 02/38568) as described in Example 1 to give 2′-fluoro-3′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-2-carbonitrile as an off-white solid (55 mg, 30%): δH (360 MHz, CDCl3) 2.36 (6H, d, J 1), 7.83 (1H, t, J 7), 8.03-8.26 (5H, m), 8.32-8.36 (1H, m), 8.39 (1H, s), 8.44 (1H, d, J 8), 8.69 (1H, q, J 4); m/z (ES+) 390 [MH+].

Sources & evidence

ORD record
ord-ece0488e29b04a82aaedd4231cb87f07
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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