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

HRID 1928057Notes

Reaction equation

HRID 1928057 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]=[N: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:5]=[N:6][CH:7]=[C:2]([C:31]4[CH:30]=[N:29][C:28]([NH2:27])=[CH:33][CH:32]=4)[CH:3]=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 686910535'-Bromo-6-cyclopropyl-4-(4-trifluoromethylphenyl)-[2,3']bipyridinyl

Product 1

HCID 686889116-Cyclopropyl-4-(4-trifluoromethyl-phenyl)-[2,3';5',3'']terpyridin-6''-ylamine

Procedure

The title compound was prepared from 5′-bromo-6-cyclopropyl-4-(4-trifluoromethyl-phenyl)-[2,3′]bipyridinyl (example E.25) (0.15 g, 0.36 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.087 g, 0.40 mmol) according to the general procedure VI. Obtained as a white solid (0.080 g, 51%). MS (ISP) 433.3 [(M+H)+]; mp 207-209° C.

Sources & evidence

ORD record
ord-d900e247a9f048838b9368496b01bfed
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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