Triethylamine → HCID 67221978, compound

HRID 876624Notes

Reaction equation

HRID 876624 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2.CCN(CC)CC.[Si:19](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Si:19]([N:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)[C:7]1=[O:11])([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 516892Sodium BicarbonateHCID 569244545-Iodo-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 67221978HCID 67221978, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 5-iodo-2,3-dihydroisoindol-1-one (3 g) in DMF (60 mL), were added N,N-dimethylaminopyridine (DMAP: 14 mg), Et3N (4.84 mL) and tert-butyl-diphenylsilyl chloride (9.0 mL). The mixture was stirred at 50° C. for 2 h. After cooling, saturated NaHCO3 aq. was added into the reaction mixture. Then it was extracted with EtOAc. The organic layer was washed with water and brine, then was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The trituration with Et2O followed by filtration gave compound aa2-1 (2.78 g) as a yellow amorphous solid.

Workup

  1. temperatureAfter cooling
  2. extractionThen it was extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialwas dried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. filtrationThe trituration with Et2O followed by filtration
  7. customgave compound aa2-1 (2.78 g) as a yellow amorphous solid

Sources & evidence

ORD record
ord-8ff25589612c4a58a373b9ac79346fe5
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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