Potassium Carbonate → 5-[2-Fluoro-6-(4-methylthiophen-2-yl)phenyl]-2-[4-(4-methylthiophen-2-yl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 508913Notes

Reaction equation

HRID 508913 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][C:10]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3Cl)=[N:9]2)=[CH:4][CH:3]=1.[CH3:22][C:23]1[CH:24]=[C:25](B(O)O)[S:26][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[F:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([C:25]2[S:26][CH:27]=[C:23]([CH3:22])[CH:24]=2)[C:14]=1[C:10]1[NH:11][C:12](=[O:13])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([C:25]3[S:26][CH:27]=[C:23]([CH3:22])[CH:24]=3)=[CH:3][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343734-Methylthiophene-2-boronic acidHCID 1366448592-(4-bromophenyl)-5-(2-chloro-6-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 1364925125-[2-Fluoro-6-(4-methylthiophen-2-yl)phenyl]-2-[4-(4-methylthiophen-2-yl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 22%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared according to the procedure described in Example-2 using 2-(4-bromophenyl)-5-(2-chloro-6-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (Intermediate-1, 0.100 g, 0.271 mmol), (4-methylthiophen-2-yl)boronic acid (0.059 g, 0.407 mmol), K2CO3 (0.112 g, 0.81 mmol), tetrakistriphenyl phosphine palladium (0) (0.062 g, 0.054 mmol) and DMSO (3.0 mL) to afford 0.020 g of desired product. 1H NMR (300 MHz, CDCl3): δ 2.29 (s, 6H), 6.86 (s, 1H), 6.91 (s, 2H), 7.13 (s, 1H), 7.21 (d, J=9.3 Hz, 1H), 7.39 (d, J=7.8 Hz, 1H), 7.48-7.55 (m, 1H), 7.61 (d, J=8.1 Hz, 2H), 7.92 (d, J=9.0 Hz, 2H), 9.27 (br s, 1H). MS (m/z): 384.88 (M−H)−.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-370e7a2f94cd4207bfe4f913c0c08cb0
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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