HCID 86680498, compound → HCID 86680499, compound

HRID 409017Notes

Reaction equation

HRID 409017 reaction equation
Br[C:2]1[S:24][C:5]2=[N:6][C:7]([Cl:23])=[C:8]([CH:10]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])[CH3:11])[CH:9]=[C:4]2[CH:3]=1>[Pd]>[Cl:23][C:7]1[N:6]=[C:5]2[S:24][CH:2]=[CH:3][C:4]2=[CH:9][C:8]=1[CH:10]([N:12]1[C:13](=[O:22])[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]1=[O:21])[CH3:11]

Participants

3

Reactant 1

HCID 86680498HCID 86680498, compound

Product 1

HCID 86680499HCID 86680499, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a hydrogenation apparatus, 2-(1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (800 mg, 1.9 mmol) and 5% palladium on carbon (151 mg) were combined. The reaction vessel was purged with nitrogen and 60 mL ethyl acetate, 15 mL ethanol, and 15 drops of concentrated HCl were added. The reaction vessel was pressurized with hydrogen gas to 50 psi. After 4 days, the apparatus was purged with nitrogen and the contents were filtered through celite. The Celite™ pad was washed with ethyl acetate to afford an orange solution. The solvent was removed on the rotovap and redissolved in dichloromethane. Silica gel (3.2 g) was added to the dichloromethane solution and the solvent was removed on the rotovap. The silica gel was transferred to the head of a chromatography column and eluted with 15% ethyl acetate in hexanes to afford 2-(1-(6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione and recovered 2-(1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. LC/MS (M+1, found=343.0). 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.82 (m, 2H), 7.72 (m, 2H), 7.54 (d, J=5.9 Hz, 1H), 7.32 (d, J=5.9 Hz, 1H), 5.95 (q, J=7.0 Hz, 1H), 1.95 (d, J=7.0 Hz, 3H) ppm.

Workup

  1. customThe reaction vessel was purged with nitrogen and 60 mL ethyl acetate, 15 mL ethanol, and 15 drops of concentrated HCl
  2. additionwere added
  3. customthe apparatus was purged with nitrogen
  4. filtrationthe contents were filtered through celite
  5. washThe Celite™ pad was washed with ethyl acetate
  6. customto afford an orange solution
  7. customThe solvent was removed on the rotovap
  8. dissolutionredissolved in dichloromethane
  9. additionSilica gel (3.2 g) was added to the dichloromethane solution
  10. customthe solvent was removed on the rotovap
  11. washeluted with 15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7459aa5586c34fe994beebf156f13f6f
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

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