Phthalimide → 2-((2S)-2-(5-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-{3-[(trimethylsilyl)ethynyl]-phenyl}propyl)-1H-isoindole-1,3(2H)-dione

HRID 339979Notes

Reaction equation

HRID 339979 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([C@@H:26]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[C:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH:31]=1)[CH2:27]O)[CH2:19]2.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([C@@H:26]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[C:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH:31]=1)[CH2:27][N:46]1[C:42](=[O:52])[C:43]3[C:44](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:45]1=[O:47])[CH2:19]2

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 866814705-bromo-2-((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)isoindolin-1-one

Product 1

HCID 866814712-((2S)-2-(5-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-{3-[(trimethylsilyl)ethynyl]-phenyl}propyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diisopropyl azodicarboxylate (0.35 mL, 1.8 mmol) in tetrahydrofuran (2.9 mL) was added 5-bromo-2-((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)-isoindolin-1-one (0.58 g, 1.3 mmol), phthalimide (0.21 g, 1.4 mmol), and triphenylphosphine (0.35 g, 1.3 mmol). The mixture was stirred at room temperature for 4 h. Direct purification by combi-flash chromatography eluting with 0-60% EtOAc in hexanes afforded the desired product. LC-MS found: 571.1 (M+H)+.

Workup

  1. customDirect purification by combi-flash chromatography
  2. washeluting with 0-60% EtOAc in hexanes

Sources & evidence

ORD record
ord-381610a7fc9547638405f9c6041056db
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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