tert-Butyl (triphenylphosphoranylidene) acetate → t-Butyl 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindoline-1-acetate

HRID 2309395Notes

Reaction equation

HRID 2309395 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([OH:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=O)=[N:9]2)=[CH:4][CH:3]=1.[C:23]([O:27][C:28]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]3[CH2:30][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 199004082-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxyisoindolin-1-one

Product 1

HCID 13655949t-Butyl 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindoline-1-acetateYield 90.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 46.0 g of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxyisoindolin-1-one, 78 g of t-butyloxycarbonylmethylenetriphenylphosphorane and 800 ml of toluene was refluxed for 5 hours. The mixture was concentrated and the residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give 54.5 g of t-butyl 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindoline-1-acetate. Recrystallization from toluene-ether gave colorless crystals melting at 210°-211° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-1a89699d12c54da7be71a7b792129730
Source dataset
uspto-grants-1987_09
Patent number
US04695572

Reaction notes

Loading…