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

HRID 1989320Notes

Reaction equation

HRID 1989320 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)[CH:7]=[C:6]([N:20]3[CH:24]=[C:23](I)[N:22]=[CH:21]3)[N:5]=2)[CH2:3][CH2:2]1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1>>[CH:1]1([C:4]2[N:5]=[C:6]([N:20]3[CH:24]=[C:23]([C:30]4[CH:31]=[CH:32][C:27]([NH2:26])=[N:28][CH:29]=4)[N:22]=[CH:21]3)[CH:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)[CH:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687412-Cyclopropyl-6-(4-iodo-imidazol-1-yl)-4-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 247602905-{1-[6-Cyclopropyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-cyclopropyl-6-(4-iodo-imidazol-1-yl)-4-(4-trifluoromethyl-phenyl)-pyridine (example E.17) (1.0 g, 2.2 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.628 g, 2.85 mmol) according to the general procedure VI. Obtained as an off-white solid (0.180 g, 46%). MS (ISP) 422.2 [(M+H)+]; mp 233-235° C.

Sources & evidence

ORD record
ord-afd025c3ab6147f4af5b972b90488398
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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