Phthalimide → HCID 86680503, compound

HRID 409029Notes

Reaction equation

HRID 409029 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:31][C:32]1[S:44][C:35]2=[N:36][C:37]([Cl:43])=[C:38]([C@H:40](O)[CH3:41])[CH:39]=[C:34]2[CH:33]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:31][C:32]1[S:44][C:35]2=[N:36][C:37]([Cl:43])=[C:38]([C@@H:40]([N:5]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])[CH3:41])[CH:39]=[C:34]2[CH:33]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86680502HCID 86680502, compound

Product 1

HCID 86680503HCID 86680503, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a reaction flask was combined phthalimide (1.530 g, 10.40 mmol), triphenylphosphine (2.73 g, 10.40 mmol), (R)-1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)-ethanol (2.15 g, 8.66 mmol) and tetrahydrofuran (57.8 mL). The reaction was cooled to 0° C. and diisopropyl azodicarboxylate (2.043 mL, 10.40 mmol) was added dropwise. The reaction was removed from the ice bath and allowed to warm to rt and stir overnight. The reaction was diluted with ethyl acetate and washed with NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. Purification using 5-10% ethyl acetate in hexanes afforded (S)-2-(1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 7.82 (m, 2H), 7.73*m, 2H), 7.18 (s, 1H), 5.90 (q, 7.3 Hz, 1H), 1.90 (d, J=7.2 Hz, 3H) ppm.

Workup

  1. customIn a reaction flask was combined
  2. customThe reaction was removed from the ice bath
  3. temperatureto warm to rt
  4. additionThe reaction was diluted with ethyl acetate
  5. washwashed with NaHCO3 and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification

Sources & evidence

ORD record
ord-13d366fd9c0f4e34ad6703a48d95b28a
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

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