Phthalimide → HCID 86680498, compound

HRID 409016Notes

Reaction equation

HRID 409016 reaction equation
[Br:1][C:2]1[S:14][C:5]2=[N:6][C:7]([Cl:13])=[C:8]([CH:10](O)[CH3:11])[CH:9]=[C:4]2[CH:3]=1.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[S:14][C:5]2=[N:6][C:7]([Cl:13])=[C:8]([CH:10]([N:19]3[C:15](=[O:25])[C:16]4[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:18]3=[O:20])[CH3:11])[CH:9]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 77230811HCID 77230811, compound

Product 1

HCID 86680498HCID 86680498, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a round-bottomed flask containing 1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethanol (2.0 g, 6.8 mmol), pthalimide (1.2 g, 8.2 mmol, 1.2 eq), and triphenylphosphine (2.15 g, 8.2 mmol) was added THF (45 mL). The solution was cooled to 0° C. and diisopropylazodicarboxylate (DIAD, 1.6 mL, 8.2 mmol, 1.2 eq) was added dropwise. The reaction was allowed to warm to room temperature. After 1 h, the reaction was judged to be complete by LC/MS. The solvent was removed in vacuo and the residue was redissolved in ether and washed with water. The water layer was back extracted with ether. The combined ether layers were washed with brine and dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography using 15% EA in hexanes to afford 2-(1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. LC/MS (M+1, found=422.8). 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 7.82 (m, 2H), 7.72 (m, 2H), 5.92 (q, J=7.0 Hz, 1H), 1.92 (d, J=7.0 Hz, 3H) ppm.

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was redissolved in ether
  4. washwashed with water
  5. extractionThe water layer was back extracted with ether
  6. washThe combined ether layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-66851e7af48c4712b36d032717a436a9
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

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