Potassium Phosphate, Tribasic → HCID 57522813, compound

HRID 1942622Notes

Reaction equation

HRID 1942622 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]([C:17]([F:20])([F:19])[F:18])[CH:8]=2)[S:4][N:3]=1.[CH2:21]([C:23]1[C:28](/[CH:29]=[CH:30]/[O:31][CH3:32])=[CH:27][CH:26]=[CH:25][C:24]=1B1OC(C)(C)C(C)(C)O1)[CH3:22].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>[CH2:21]([C:23]1[C:28](/[CH:29]=[CH:30]/[O:31][CH3:32])=[CH:27][CH:26]=[CH:25][C:24]=1[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]([C:17]([F:20])([F:19])[F:18])[CH:8]=2)[S:4][N:3]=1)[CH3:22]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 57522699HCID 57522699, compoundHCID 669817762-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 57522813HCID 57522813, compoundYield 97.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-bromo-5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-thiadiazole (D45) (487 mg), 2-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (573 mg) and tripotassium phosphate (845 mg) in N,N-dimethylformamide (DMF) (4 mL) and water (0.800 mL) stirred under nitrogen at room temp was added Pd(Ph3P)4 (153 mg). The reaction mixture was sealed and heated under microwave at 120° C. for 10 min. After cooling the reaction, the mixture was concentrated and purified by column chromatography to give 3-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-thiadiazole (D49) (580 mg) as a colorless oil. MS (ES): C23H23F3N2O2S requires 448. found 449.1 (M+H+).

Workup

  1. customThe reaction mixture was sealed
  2. temperatureAfter cooling
  3. customthe reaction
  4. concentrationthe mixture was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-ce847163fbe54c3694d1fb8588615139
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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