3-Bromo-2,4-difluoroaniline → 3'-Amino-6,2',6'-trifluorobiphenyl-2-carbonitrile

HRID 1180251Notes

Reaction equation

HRID 1180251 reaction equation
Br[C:2]1[C:3]([F:10])=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[F:8].[F:11][C:12]1[C:13](B2OC(C)(C)C(C)(C)O2)=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16]>>[NH2:9][C:4]1[C:3]([F:10])=[C:2]([C:13]2[C:14]([C:15]#[N:16])=[CH:17][CH:18]=[CH:19][C:12]=2[F:11])[C:7]([F:8])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 137327463-Bromo-2,4-difluoroanilineHCID 222401043-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 222400923'-Amino-6,2',6'-trifluorobiphenyl-2-carbonitrileYield 25%

Procedure

3-Bromo-2,4-difluorophenylamine and 3-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile were coupled together as described in Example 2 to give 3′-amino-6,2′,6′-trifluorobiphenyl-2-carbonitrile as an off-white solid (400 mg, 25%): δH (360 MHz, CDCl3) 6.88 (2H, s), 7.41-7.46 (1H, m), 7.50-7.56 (1H, m), 7.61 (1H, dd, J 7 and 1).

Sources & evidence

ORD record
ord-cf9cf61dd2704877b6047c54aa5f1b1b
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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