Potassium Phosphate, Tribasic → 5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazole

HRID 1942671Notes

Reaction equation

HRID 1942671 reaction equation
Br[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[C:9]([Cl:17])[CH:8]=2)[S:4][N:3]=1.[CH3:18][O:19][C:20]1[C:25](/[CH:26]=[CH:27]/[O:28][CH3:29])=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:9]1[CH:8]=[C:7]([C:5]2[S:4][N:3]=[C:2]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25](/[CH:26]=[CH:27]/[O:28][CH3:29])[C:20]=3[O:19][CH3:18])[N:6]=2)[CH:12]=[CH:11][C:10]=1[O:13][CH:14]([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 584940863-Bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazoleHCID 58494144{2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}boronic acid

Product 1

HCID 584941155-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazoleYield 60.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazole (D43) (200 mg, 0.599 mmol), {2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}boronic acid (D101) (187 mg, 0.899 mmol), tripotassium phosphate (318 mg, 1.499 mmol) and Pd(Ph3P)4 (69.3 mg, 0.060 mmol) in N,N-Dimethylformamide (DMF) (5 mL) and Water (2 mL) was stirred at 120° C. (Microwave) for 10 min. The reaction mixture was poured to water. Then the mixture was extracted with EA. The combined organic layers were washed with water and then dried over anhydrous sodium sulphate. After filtration and concentration, the residue was purified by column chromatography to give 5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazole (D102) (152 mg). MS (ES): C21H21ClN2O3S requires 416.1. found 417.1 (M+H+).

Workup

  1. extractionThen the mixture was extracted with EA
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bdf4d4f2a6e04324a7fffe1bcd15aafc
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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