4-Hydroxymethylpyridine → 2-(4-t-Butyl-phenyl)-7-(pyridin-4-ylmethoxy)-2,3-dihydro-isoindol-1-one

HRID 2251852Notes

Reaction equation

HRID 2251852 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:19][C:18]3[C:13](=[C:14]([OH:20])[CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O[CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.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>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:19][C:18]3[C:13](=[C:14]([O:20][CH2:23][C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 690313142-(4-t-Butyl-phenyl)-7-hydroxy-2,3-dihydro-isoindol-1-one

Product 1

HCID 111996002-(4-t-Butyl-phenyl)-7-(pyridin-4-ylmethoxy)-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-t-Butyl-phenyl)-7-hydroxy-2,3-dihydro-isoindol-1-one (0.201 g), 4-hydroxymethylpyridine (96 mg) and PPh3 (0.212 g) were dissolved in THF (20 mL). DIAD (0.16 mL) was added and the mixture was stirred at RT for 2 h. Solvent was evaporated and the residue was purified by silica gel chromatography (70 g, 100% EtOAc) to afford 2-(4-t-butyl-phenyl)-7-(pyridin-4-ylmethoxy)-2,3-dihydro-isoindol-1-one as a white solid. MS: (ES+) 373(M+H). Calc'd. for C24H24N2O2-372.46.

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by silica gel chromatography (70 g, 100% EtOAc)

Sources & evidence

ORD record
ord-199d0d05e3754769bdc0be1b632f72e1
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

Loading…