4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → 3'-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-4-ylamine

HRID 1928101Notes

Reaction equation

HRID 1928101 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:36]2[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=2)O1>>[F:15][C:14]([F:17])([F:16])[C:12]1[CH:11]=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([C:36]3[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=3)[CH:7]=[CH:6][CH:5]=2)[N:13]=1

Participants

3

Reactant 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 574687272-(3-Bromo-phenyl)-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyrimidine

Product 1

HCID 602093963'-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-4-ylamine

Procedure

The title compound was prepared from 2-(3-bromo-phenyl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (example E.3) (0.22 g, 0.5 mmol) and commercially available 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.13 g, 0.59 mmol) according to the general procedure VI. Obtained as a light yellow solid (0.174 g, 76%). MS (ISP) 460.3 [(M+H)+]; mp 186° C.

Sources & evidence

ORD record
ord-52fa4fedec5d4806b06c80f9400c9af4
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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