Triethylsilane → HCID 84733318, compound

HRID 2277607Notes

Reaction equation

HRID 2277607 reaction equation
C([SiH](CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[NH:13][C:12]2([CH2:20][CH3:21])O.ClC1C=C2C(C(CC)(O)NC2=O)=CC=1>C(O)(C(F)(F)F)=O>[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[NH:13][CH:12]2[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 866859341H-Isoindol-1-one, 5-chloro-3-ethyl-2,3-dihydro-3-hydroxy-HCID 86685935HCID 86685935, compound

Product 1

HCID 84733318HCID 84733318, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Under N2 protection, triethylsilane (19.3 g, 166 mmol) and TFA (20 mL) were added successively to a mixture of 5-chloro-3-ethyl-3-hydroxy-2,3-dihydro-isoindol-1-one and 6-chloro-3-ethyl-3-hydroxy-2,3-dihydro-isoindol-1-one (3.52 g, 16.6 mmol). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with a satd. aq. solution of NaHCO3 (30 mL) and extracted with DCM (2×30 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude mixture of products. The desired regioisomer, 5-chloro-3-ethyl-2,3-dihydro-isoindol-1-one was obtained by prep-HPLC separation as a white solid (0.65 g, 20%). MS: 196.1 (M+H+).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was treated with a satd
  3. extractionaq. solution of NaHCO3 (30 mL) and extracted with DCM (2×30 mL)
  4. washThe combined organic layers were washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customto give a crude
  9. additionmixture of products

Sources & evidence

ORD record
ord-c7c91bd463b74495b5b82466dda15e36
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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