3-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester → HCID 90404419, compound

HRID 1772416Notes

Reaction equation

HRID 1772416 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][C:34]([O:36][CH3:37])=[O:35])[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][C:34]([O:36][CH3:37])=[O:35])[CH:27]=[CH:26][CH:31]=3)=[N:3]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 574434813-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl esterHCID 712094283-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 90404419HCID 90404419, 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), methyl 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate (C13a), and [1,1′-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) at 80° C. and isolated as a dark orange solid (9.86 g, 91%): 1H NMR (400 MHz, DMSO-d6) δ 9.40 (s, 1H), 8.12-8.03 (m, 2H), 8.01-7.91 (m, 2H), 7.66-7.58 (m, 2H), 7.49-7.40 (m, 1H), 7.34 (dt, J=7.8, 1.6 Hz, 1H), 3.59 (s, 3H), 2.95 (t, J=7.5 Hz, 2H), 2.70 (t, J=7.6 Hz, 2H); 19F NMR (376 MHz, DMSO-d6) δ −57.01; ESIMS m/z 392 ([M+H]+).

Sources & evidence

ORD record
ord-c762baee973148d2b4d4c2c01085019c
Source dataset
uspto-grants-2016_02
Patent number
US09249133B2

Reaction notes

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