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

HRID 1928281Notes

Reaction equation

Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:10]=[C:9]([CH3:23])[N:8]=2)=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][N:26]=1>>[CH3:23][C:9]1[N:8]=[C:7]([C:5]2[S:6][C:2]([C:28]3[CH:29]=[CH:30][C:25]([NH2:24])=[N:26][CH:27]=3)=[CH:3][CH:4]=2)[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:10]=1

Participants

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

HCID 574688002-(5-Bromo-thiophen-2-yl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 247605105-{5-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiophen-2-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-(5-bromo-thiophen-2-yl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.86) (0.27 g, 0.678 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.164 g, 0.745 mmol) according to the general procedure VI. Obtained as a light brown solid (0.100 g, 35%). MS (ISP) 412.2 [(M+H)+]; mp 196° C.

Sources & evidence

ORD record: ord-4b212e8fcaf6455fa29a8eae846ae697
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183262B2

Reaction notes

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