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

HRID 1928052Notes

Reaction equation

HRID 1928052 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]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH:24]3[CH2:26][CH2:25]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1>>[CH:24]1([C:10]2[N:9]=[C:8]([C:4]3[CH:3]=[C:2]([C:31]4[CH:32]=[CH:33][C:28]([NH2:27])=[N:29][CH:30]=4)[CH:7]=[CH:6][CH:5]=3)[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=2)[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687462-(3-Bromo-phenyl)-6-cyclopropyl-4-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 602093745-{3-[6-Cyclopropyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-phenyl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-(3-bromo-phenyl)-6-cyclopropyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.22) (0.30 g, 0.55 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.219 g, 0.94 mmol) according to the general procedure VI. Obtained as an off-white solid (0.250 g, 80%). MS (ISP) 432.3 [(M+H)+]; mp 130-135° C.

Sources & evidence

ORD record
ord-09eff0bcee4f41328d55f64a517fcfab
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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