2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → 2'-Fluoro-5'-(7-isopropylimidazo[1,2-alpha]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 2183871Notes

Reaction equation

HRID 2183871 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]([CH3:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][C:16]=1[C:30]1[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=1>>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([CH:11]([CH3:13])[CH3:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:17][C:16]=1[C:30]1[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrileHCID 180012843-Bromo-7-isopropylimidazo[1,2-a]pyrimidine

Product 1

HCID 101329152'-Fluoro-5'-(7-isopropylimidazo[1,2-alpha]pyrimidin-3-yl)biphenyl-2-carbonitrile

Procedure

3-Bromo-7-isopropylimidazo[1,2-α]pyrimidine was coupled with 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 2′-fluoro-5′-(7-isopropylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile as an off-white powder: δH (360 MHz, CDCl3) 1.38 (6H, d, J 7), 3.15 (1H, septet, J 7), 6.87 (1H, d, J 7), 7.39 (1H, t, J 9), 7.52-7.63 (4H, m), 7.71 (1H, dd, J 8 and 1), 7.83 (2H, dd, J 8 and 7), 8.74 (1H, d, J 7); m/z (ES+) 357 (M++H).

Sources & evidence

ORD record
ord-49a3ec6386e547a8aec175704da9dd12
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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