Water → 3-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylbenzaldehyde

HRID 1942589Notes

Reaction equation

HRID 1942589 reaction equation
Br[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[C:9]([Cl:17])[CH:8]=2)=[N:5][N:6]=1.[CH2:18]([C:20]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[O:23])[CH3:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C)C=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:4]2[S:3][C:2]([C:27]3[C:20]([CH2:18][CH3:19])=[C:21]([CH:24]=[CH:25][CH:26]=3)[CH:22]=[O:23])=[N:6][N:5]=2)[CH:12]=[CH:11][C:10]=1[O:13][CH:14]([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 575060202-Bromo-5-[3-chloro-4-(1-methylethoxy)phenyl]-1,3,4-thiadiazoleHCID 584940852-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Product 1

HCID 584940093-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylbenzaldehydeYield 28.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 178418397HCID 178418397, compoundSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of 2-bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazole (D10) (0.5 g), 2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (D5) (0.468 g) and tripotassium phosphate (0.795 g) in N,N-dimethylformamide (DMF) (10 mL) and Pd(Ph3P)4 (0.173 g). The reaction mixture was degassed and then the reaction vial was sealed and heated under microwave at 130° C. for 10 min. Water was then added to the reaction mixture. The mixture was extracted with EA. The combined organic solution was dried over anhydrous sodium sulphate. After filtration and concentration, the residue was purified by column chromatography to give 3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylbenzaldehyde (D11) (164 mg). MS (ES): C20H19ClN2O2S requires 386. found 387.1 (M+H+).

Workup

  1. customThe reaction mixture was degassed
  2. customthe reaction
  3. customvial was sealed
  4. extractionThe mixture was extracted with EA
  5. dry with materialThe combined organic solution was dried over anhydrous sodium sulphate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2369afa577f949ec92b4b55a43842858
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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