Phthalimide → HCID 71272451, compound

HRID 475288Notes

Reaction equation

HRID 475288 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.[H-].[Na+].Br[CH:15]([C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[CH:20][N:21]2[S:26]([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH3:16]>CN(C=O)C>[S:26]([N:21]1[C:22]2[C:18](=[C:17]([CH:15]([N:2]3[C:3](=[O:10])[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:1]3=[O:11])[CH3:16])[CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:20]1)([C:29]1[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=1)(=[O:27])=[O:28]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 24758Sodium hydrideHCID 22155939HCID 22155939, compound

Product 1

HCID 71272451HCID 71272451, compoundYield 112.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of isoindoline-1,3-dione (3.83 g, 20.0 mmol), in dry DMF (70 mL) at 0° C. under argon was added NaH (1.04 g, 26 mmol). The resultant mixture was stirred at RT for 30 min. A solution of 284 (9.8 g, 26 mmol) in dry DMF (30 mL) was added and the mixture was stirred at RT for 4 h. The mixture was concentrated in vacuo and purified by SiO2 chromatography to afford 10 g (86%) of 2-(1-(1-tosyl-1H-indol-4-yl)ethyl)isoindoline-1,3-dione (286) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 7.87-7.81 (m, 8H), 7.48 (d, J=7.6 Hz, 1H), 7.38-7.33 (m, 3H), 6.82 (d, J=3.6 Hz, 1H), 5.77-5.74 (m, 1H), 2.29 (s, 3H), 1.84 (d, J=6.8 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by SiO2 chromatography

Sources & evidence

ORD record
ord-678d84e5bfed4bb7a88ec80b6b6ec8f8
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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