2-[2-(Pyridin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione → HCID 68579670, compound

HRID 645913Notes

Reaction equation

HRID 645913 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:39]2([OH:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32](=[O:41])[N:31]2[CH2:30][CH2:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)=[CH:11][C:10]=1[O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2313802-[2-(Pyridin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dioneHCID 36131281-(Benzyloxy)-4-bromo-2-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 68579670HCID 68579670, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2 (4.0 g, 13.7 mmol) in dry THF (40 mL) at −78° C. was treated with n-BuLi (2.5 M, 6.0 mL, 15.0 mmol) for 15 min to produce 3. To this solution, 5 (3.1 g, 12.2 mmol) in dry THF (40 mL) was added slowly over a 10 min period. The reaction mixture turned light brown in color and stirring was continued for 1 h. The reaction was quenched by the addition of saturated aqueous NH4Cl (10 mL) and the organic layer was separated. The aqueous layer was extracted with EtOAc (3×25 mL) and the combined organic layer was washed with brine (15 mL). Volatiles were evaporated under reduced pressure and the crude residue was purified by column chromatography using 20% acetone/hexane as the eluent to afford the title compound 6 as a white solid (2.6 g, 46%).

Workup

  1. customto produce 3
  2. customThe reaction was quenched by the addition of saturated aqueous NH4Cl (10 mL)
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
  5. washthe combined organic layer was washed with brine (15 mL)
  6. customVolatiles were evaporated under reduced pressure
  7. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-dd32ed568b1744cea450e2fb0ed1196a
Source dataset
uspto-grants-2010_04
Patent number
US07705021B2

Reaction notes

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