Phthalimide → HCID 58318591, compound

HRID 473407Notes

Reaction equation

HRID 473407 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH:18](O)[CH3:19])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][N:14]=2)[N:9]=1.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH:18]([N:25]2[C:21](=[O:31])[C:22]3[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:24]2=[O:26])[CH3:19])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][N:14]=2)[N:9]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58318644HCID 58318644, compound

Product 1

HCID 58318591HCID 58318591, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-(2-Fluorophenyl)-1,5-naphthyridin-3-yl)ethanol (550 mg, 2.04 mmol) and phthalimide (600 mg, 4.09 mmol) were dissolved in THF (20 mL) and the mixture was cooled to 0° C. To the cooled mixture was added PPh3 (1.07 g, 4.09 mmol) and the mixture was stirred for 5-10 min at 0° C. Then DIAD (800 mg, 4.09 mmol) was added dropwise to the above reaction mixture at 0° C., and the reaction mixture was slowly allowed to warm to rt and maintained at rt for 3 h. After completion of reaction, the reaction mixture was quenched with water and ethyl acetate. The organic layer was separated and the aqueous layer was back extracted with ethyl acetate. The organic layers were combined and dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 2-(1-(2-(2-fluorophenyl)-1,5-naphthyridin-3-yl)ethyl)-1H-isoindole-1,3(2H)-dione as a white solid: 1H-NMR (CDCl3) δ: 1.8 (s, 3H), 5.0 (brs, 1H), 6.4 (s, 2H), 7.7-7.2 (m, 7H), 8.4 (d, 1H), 9.0-8.8 (d, 2H).

Workup

  1. temperatureto warm to rt
  2. temperaturemaintained at rt for 3 h
  3. customAfter completion of reaction
  4. customthe reaction mixture was quenched with water and ethyl acetate
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was back extracted with ethyl acetate
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03e49404ef1c4b098988ffa56496c872
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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