Phthalimide → 2-((4,5-Bis(4-methoxybenzyloxy)pyridin-2-yl)methyl)isoindoline-1,3-dione

HRID 627114Notes

Reaction equation

HRID 627114 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([CH2:25]O)[CH:10]=2)=[CH:5][CH:4]=1.[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([CH2:25][N:33]3[C:29](=[O:39])[C:30]4[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:32]3=[O:34])[CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 156625066-Hydroxymethyl-3,4-bis[(p-methoxybenzyl)oxy]-pyridine2×

Product 1

HCID 898519332-((4,5-Bis(4-methoxybenzyloxy)pyridin-2-yl)methyl)isoindoline-1,3-dioneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4,5-bis(4-methoxybenzyloxy)pyridin-2-yl)methanol (Intermediate 63, 1.5 g, 3.93 mmol), phthalimide (0.579 g, 3.93 mmol) and triphenylphosphine (1.028 g, 3.93 mmol) in THF (15 mL) at room temperature was added diisopropyl azodicarboxylate (2.091 mL, 10.62 mmol). The reaction was stirred at room temperature overnight then concentrated onto silica gel. Silica gel chromatography (0%-70% ethyl acetate) afforded the title compound as a light brown solid (1.1 g, 55%).

Workup

  1. concentrationthen concentrated onto silica gel

Sources & evidence

ORD record
ord-e49898efbc684971bc735b83cb03239a
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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