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 1180241Notes

Reaction equation

HRID 1180241 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:38]#[N:39])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25](B3OC(C)(C)C(C)(C)O3)[CH:24]=2)=[CH:21][CH:22]=1>>[F:16][C:17]1[CH:18]=[C:19]([C:38]#[N:39])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:2]3[N:6]4[CH:7]=[CH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]4=[N:4][CH:3]=3)[CH:24]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 222853364-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 104304094-Fluoro-3'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrileYield 53.5%

Procedure

3-Bromo-8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridine (0.10 g, 0.36 mmol) and 4-fluoro-3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (0.15 g, 0.47 mmol) were coupled following the procedure in Example 1 to afford 4-fluoro-3′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-2-carbonitrile as a white amorphous solid (75 mg, 53%): δH (360 MHz, CDCl3) 1.74 (6H, s), 2.09 (1H, s), 7.19 (1H, dd, J 7 and 7), 7.30 (1H, ddd,J 8, 8 and 3), 7.49-7.58 (3H, m), 7.64-7.66 (2H, m), 7.73-7.75 (2H, m), 8.33 (1H, d, J 7); m/z (ES+) 390 (M++H).

Sources & evidence

ORD record
ord-dceb491b091747ea818b044ab773b684
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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