5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → 5-{3-[4-(4-Chloro-phenyl)-6-trifluoromethyl-pyridin-2-yl]-phenyl}-pyridin-2-ylamine

HRID 1989542Notes

Reaction equation

HRID 1989542 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:11]=[C:10]([C:21]([F:24])([F:23])[F:22])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=1>>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:11]=[C:10]([C:21]([F:24])([F:23])[F:22])[N:9]=[C:8]([C:4]3[CH:3]=[C:2]([C:29]4[CH:30]=[CH:31][C:26]([NH2:25])=[N:27][CH:28]=4)[CH:7]=[CH:6][CH:5]=3)[CH:13]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687962-(3-Bromo-phenyl)-4-(4-chloro-phenyl)-6-trifluoromethyl-pyridine

Product 1

HCID 602094565-{3-[4-(4-Chloro-phenyl)-6-trifluoromethyl-pyridin-2-yl]-phenyl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-(3-bromo-phenyl)-4-(4-chloro-phenyl)-6-trifluoromethyl-pyridine (example E.82) (0.30 g, 0.727 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.192 g, 0.873 mmol) according to the general procedure VI. Obtained as a light grey solid (0.200 g, 65%). MS (ISP) 426.0 [(M+H)+] and 428 [(M+2+H)+]; mp 172° C.

Sources & evidence

ORD record
ord-7d4fa07dff934c79aed0c18af6fbd813
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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