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

HRID 1928067Notes

Reaction equation

HRID 1928067 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH:19]=[C:18](I)[N:17]=[CH:16]3)[CH:9]=2)=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][N:23]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH:19]=[C:18]([C:25]4[CH:26]=[CH:27][C:22]([NH2:21])=[N:23][CH:24]=4)[N:17]=[CH:16]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687494-(4-Chloro-phenyl)-2-(4-iodo-imidazol-1-yl)-6-methyl-pyridine

Product 1

HCID 247603615-{1-[4-(4-Chloro-phenyl)-6-methyl-pyridin-2-yl]-1H-imidazol-4-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 4-(4-chloro-phenyl)-2-(4-iodo-imidazol-1-yl)-6-methyl-pyridine (example E.30) (0.200 g, 0.51 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.122 g, 0.62 mmol) according to the general procedure VI. Obtained as a white solid (0.035 g, 19%). MS (ISP) 362.3 [(M+H)+] and 364 [(M+2+H)+]; mp 230-233° C.

Sources & evidence

ORD record
ord-c542a021e2254409b412b6f5907bd10c
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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