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

HRID 1989281Notes

Reaction equation

HRID 1989281 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:10]=[C:9]([C:20]([F:23])([F:22])[F:21])[N:8]=2)[CH:6]=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][N:26]=1>>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:10]=[C:9]([C:20]([F:23])([F:22])[F:21])[N:8]=[C:7]([N:5]3[CH:6]=[C:2]([C:28]4[CH:29]=[CH:30][C:25]([NH2:24])=[N:26][CH:27]=4)[N:3]=[CH:4]3)[N:12]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687262-(4-Bromo-imidazol-1-yl)-4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidine

Product 1

HCID 602093485-{1-[4-(4-Chloro-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-(4-bromo-imidazol-1-yl)-4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidine (example E.2) (0.40 g, 1.0 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.22 g, 1.0 mmol) according to the general procedure VI. Obtained as a yellow solid (0.095 g, 23%). MS (ISP) 417.3 [(M+H)+]; mp 254° C.

Sources & evidence

ORD record
ord-4e6c2758cab44af696bd351cbed05dd0
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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