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

HRID 1942617Notes

Reaction equation

HRID 1942617 reaction equation
[Br:1][C:2]1[N:6]=[C:5](Cl)[S:4][N:3]=1.[Cl:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:1][C:2]1[N:6]=[C:5]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH:16]([CH3:17])[CH3:18])=[C:9]([Cl:8])[CH:10]=2)[S:4][N:3]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27250533-Bromo-5-chloro-1,2,4-thiadiazoleHCID 33824673-Chloro-4-isopropoxyphenylboronic acid

Product 1

HCID 584940863-Bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazoleYield 96.4%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-bromo-5-chloro-1,2,4-thiadiazole (558 mg), {3-chloro-4-[(1-methylethyl)oxy]phenyl}boronic acid (300 mg) and tripotassium phosphate (148 mg) in N,N-dimethylformamide (DMF) (3 mL) and water (0.600 mL) under nitrogen was added PdCl2(dppf)-CH2Cl2 adduct (3.427 g). The reaction vessel was sealed and heated under microwave at 80° C. for 1 h. After cooling the reaction, the mixture was filtered and the filtrate was diluted with ethyl acetate (50 mL), washed with brine (2*10 mL), dried over sodium sulphate, concentrated and purified by column chromatography to afford 3-bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazole (D43) (450 mg) as a clear oil. MS (ES): C11H10BrClN2OS requires 332. found 333.0 (M+H+).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe reaction
  4. filtrationthe mixture was filtered
  5. additionthe filtrate was diluted with ethyl acetate (50 mL)
  6. washwashed with brine (2*10 mL)
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-79a3ca816d044bae80e79e5ac40800f7
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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