Phthalimide → 2-((2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dione

HRID 623462Notes

Reaction equation

HRID 623462 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[C:5]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:4]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])=[CH:7][CH:6]=[C:5]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:4]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 67509554(2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanol

Product 1

HCID 675086782-((2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dioneYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanol (1.19 g, 5.02 mmol, Step-2), phthalimide (0.74 g, 5.02 mmol), di-tert-butyl azodicarboxylate (1.05 g, 6.02 mmol) and triphenylphosphine (1.97 g, 7.53 mmol) in tetrahydrofuran (50 mL) is stirred at room temperature for 20 hours. The reaction mixture is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (6:1) to give 0.67 g (37% yield) of the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-1d1aef006f154b83b0e21169cc08d048
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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