3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole → HCID 90403940, compound

HRID 573816Notes

Reaction equation

HRID 573816 reaction equation
Br[C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[C:28]([CH2:32][CH2:33][CH2:34][CH2:35][N:36]3[C:44](=[O:45])[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:37]3=[O:46])[CH:29]=[CH:30][CH:31]=2)O1>CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.Cl[Pd]Cl.[Fe]>[F:15][C:14]([F:17])([F:16])[O:13][C:10]1[CH:11]=[CH:12][C:7]([N:4]2[CH:5]=[N:6][C:2]([C:30]3[CH:29]=[C:28]([CH2:32][CH2:33][CH2:34][CH2:35][N:36]4[C:37](=[O:46])[C:38]5[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:44]4=[O:45])[CH:27]=[CH:26][CH:31]=3)=[N:3]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 712094283-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazoleHCID 90404701HCID 90404701, compound

Product 1

HCID 90403940HCID 90403940, compound

Reagents, catalysts & solvents 1

HCID 178454869HCID 178454869, compoundCatalyst

Procedure

The title compound was prepared as described in Example 10 using 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C1), 2-(4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)isoindoline-1,3-dione (C13b), and [1,1′-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) at 75° C. and isolated as a dark orange solid (5.48 g, 82%): 1H NMR (400 MHz, DMSO-d6) δ 9.39 (s, 1H), 8.13-8.04 (m, 2H), 7.96-7.89 (m, 2H), 7.88-7.77 (m, 4H), 7.67-7.57 (m, 2H), 7.45-7.38 (m, 1H), 7.31 (dt, J=7.7, 1.5 Hz, 1H), 3.69-3.53 (m, 2H), 2.70 (t, J=6.8 Hz, 2H), 1.64 (dq, J=6.6, 3.1 Hz, 4H); 19F NMR (376 MHz, DMSO-d6) δ −56.97; ESIMS m/z 507 ([M+H]+).

Sources & evidence

ORD record
ord-519e3e723c084147b820400f8544065b
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

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