2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 9968066, compound

HRID 2183900Notes

Reaction equation

HRID 2183900 reaction equation
Br[C:2]1[N:6]2[CH:7]=[C:8]([F:12])[C:9]([CH3:11])=[N:10][C:5]2=[N:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][C:15]=1[C:29]1[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=1>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[N:6]3[CH:7]=[C:8]([F:12])[C:9]([CH3:11])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:16][C:15]=1[C:29]1[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=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 69708445HCID 69708445, compound

Product 1

HCID 9968066HCID 9968066, compoundYield 58%

Procedure

3-Bromo-6-fluoro-7-methylimidazo[1,2-α]pyrimidine (24 mg, 0.50 mmol) 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′-(6-fluoro-7-methylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile (21 mg, 58%) as a white powder: δH (400 MHz, CDCl3) 2.67 (3H, d, J 3), 7.39-7.43 (1H, m), 7.53-7.62 (4H, m), 7.69-7.74 (1H, m), 7.84 (1H, d, J 1), 7.86 (1H, s), 8.67 (1H, d, J 5); m/z (ES+) 347 (M++H).

Sources & evidence

ORD record
ord-84a09928145f4c6e8a4d3dd352c3771c
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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