2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 9924945, compound

HRID 2183886Notes

Reaction equation

HRID 2183886 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][CH3:13])=[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]([CH2:11][O:12][CH3:13])=[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 69707932HCID 69707932, compound

Product 1

HCID 9924945HCID 9924945, compoundYield 60%

Procedure

3-Bromo-7-methoxymethylimidazo[1,2-α]pyrimidine (121 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′-(7-methoxymethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile (108 mg, 60%) as a white powder: δH (400 MHz, CDCl3) 3.50 (3H, s), 4.66 (2H, s), 7.19 (1H, d, J 7), 7.39-7.41 (1H, m), 7.53-7.64 (4H, m), 7.69-7.73 (1H, m), 7.85 (1H, dd, J 8 and 1), 7.87 (1H, s), 8.82 (1H, d, J 7); m/z (ES+) 359 (M++H).

Sources & evidence

ORD record
ord-0837dc64006047a8a6e072d22cc9e769
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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