Phthalimide → (+/-)-2-(1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl)isoindoline-1,3-dione

HRID 2099764Notes

Reaction equation

HRID 2099764 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:31][C:32]1[N:37]=[C:36]([CH:38](O)[CH2:39][C:40]2[CH:48]=[C:47]([CH3:49])[C:46]3[C:42](=[CH:43][N:44]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[N:45]=3)[CH:41]=2)[CH:35]=[CH:34][CH:33]=1>C(Cl)Cl.CCCCCC>[Br:31][C:32]1[N:37]=[C:36]([CH:38]([N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH2:39][C:40]2[CH:48]=[C:47]([CH3:49])[C:46]3[C:42](=[CH:43][N:44]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[N:45]=3)[CH:41]=2)[CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 57794705(+/-)-1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanol

Product 1

HCID 57794614(+/-)-2-(1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl)isoindoline-1,3-dioneYield 118.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of phthalimide (294 mg, 2 mmol) and triphenylphosphine (525 mg, 2 mmol) in anhydrous methylene chloride (10 mL) was added via syringe to (±)-1-(6-bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanol (460 mg, 1 mmol). To the resulting suspension was then added diisopropylazidodicarboxylate (0.3 mL, 1.5 mmol) under nitrogen at room temperature via syringe. The resulting mixture was stirred at room temperature overnight (17 h). The mixture was diluted with hexane and purified by flash column chromatography to give a light yellow oil (700 mg, 100%). MS (ESI) [M+H]+=592. HPLC tR=2.05 min.

Workup

  1. customat room temperature
  2. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-a36d909fd9ca497bbb7c334da9b1707b
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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