Potassium Phosphate, Tribasic → HCID 66981731, compound

HRID 1942606Notes

Reaction equation

HRID 1942606 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[C:11]([CH:14]=2)[C:12]#[N:13])=[N:4][N:3]=1.[CH2:19]([C:21]1[C:26](/[CH:27]=[CH:28]/[O:29][CH3:30])=[CH:25][CH:24]=[CH:23][C:22]=1B1OC(C)(C)C(C)(C)O1)[CH3:20].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>[CH2:19]([C:21]1[C:26](/[CH:27]=[CH:28]/[O:29][CH3:30])=[CH:25][CH:24]=[CH:23][C:22]=1[C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[C:11]([CH:14]=2)[C:12]#[N:13])=[N:4][N:3]=1)[CH3:20]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 669817762-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 669818275-(5-Bromo-1,3,4-thiadiazol-2-yl)-2-(2-methylpropyl)benzonitrile

Product 1

HCID 66981731HCID 66981731, compoundYield 97.8%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

To a suspension of 5-(5-bromo-1,3,4-thiadiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D26) (151 mg), 2-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (203 mg) and tripotassium phosphate (249 mg) in N,N-dimethylformamide (DMF) (6 mL) and water (1.5 mL) under nitrogen was added Pd(Ph3P)4 (54.2 mg). The reaction vessel was sealed and heated under microwave at 120° C. for 10 min. Water was added. The reaction mixture was extracted with EA for 3 times, the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, the dried solution was concentrated, and purified by column chromatography to afford 5-(5-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,3,4-thiadiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D30) (185 mg) as a yellow oil. MS (ES): C24H25N3OS requires 403. found 404.2 (M+H+).

Workup

  1. customThe reaction vessel was sealed
  2. extractionThe reaction mixture was extracted with EA for 3 times
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationthe dried solution was concentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-5150eee90abc46909a2e1f4bbc54267d
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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