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

HRID 1180247Notes

Reaction equation

HRID 1180247 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:18]=[C:19]([C:32]2[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=1>>[F:16][C:17]1[CH:18]=[C:19]([C:32]2[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:20]=[C:21]([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:22]=1

Participants

3

Reactant 2

HCID 116742013'-Fluoro-5'-(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 104080043'-Fluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrileYield 51%

Procedure

2-(3-Bromo-8-fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 3′-fluoro-5′-(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 3′-fluoro-5′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-2-carbonitrile as an off-white solid (200 mg, 51%): δH (360 MHz, CDCl3) 1.74 (6H, s), 2.13 (1H, s), 7.24 (1H, s), 7.27-7.29 (1H, m), 7.34-7.37 (1H, m), 7.51-7.58 (3H, m), 7.69-7.73 (1H, m), 7.76 (1H, s), 7.84 (1H, dd, J 8 and 1), 8.39 (1H, d, J 7); m/z (ES+) 390 [MH+].

Sources & evidence

ORD record
ord-18ec943ab8e04dbbb46dcd7c88e04823
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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