2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 10132344, compound

HRID 2183898Notes

Reaction equation

HRID 2183898 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH2:11][F:12])=[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]=[CH:8][C:9]([CH2:11][F:12])=[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 69708312HCID 69708312, compound

Product 1

HCID 10132344HCID 10132344, compoundYield 67%

Procedure

3-Bromo-7-fluoromethylimidazo[1,2-α]pyrimidine (115 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-fluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile (116 mg, 67%) as a white powder: δH (400 MHz, CDCl3) 5.57 (2H, d, J 47), 7.20 (1H, dd, J 7 and 1), 7.42 (1H, dt, J 9 and 1), 7.55 (1H, dt, J 8 and 1), 7.60-7.66 (3H, m), 7.70-7.74 (1H, m), 7.85 (1H, dd, J 8 and 1), 7.90 (1H, s), 8.91 (1H, d, J 7); m/z (ES+) 347 (M++H).

Sources & evidence

ORD record
ord-52823fad21ff41e78c8292a39bec5592
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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