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

HRID 1928048Notes

Reaction equation

HRID 1928048 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:28][C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1>>[F:16][C:14]([F:15])([F:17])[C:12]1[CH:11]=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:20][CH:19]=2)[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([C:32]3[CH:33]=[CH:34][C:29]([NH2:28])=[N:30][CH:31]=3)[CH:7]=[CH:6][CH:5]=2)[CH:13]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687442-(3-Bromo-phenyl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 602093725-{3-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-phenyl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-(3-bromo-phenyl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine (example E.20) (0.525 g, 1.0 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.286 g, 1.3 mmol) according to the general procedure VI. Obtained as a white solid (0.10 g, 22%). MS (ISP) 460.2 [(M+H)+]; mp 170-172° C.

Sources & evidence

ORD record
ord-3ce009b53e97455b82af3fe9538aef83
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

Loading…