1,4-Dioxane → HCID 68448192, compound

HRID 1186268Notes

Reaction equation

HRID 1186268 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:6]=[C:5]2B(O)O.[CH3:21][N:22]1[C:26](=[O:27])[CH:25]=[CH:24][C:23]1=[O:28].O1CCOCC1>[Rh].O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:6]=[C:5]2[CH:24]1[CH2:25][C:26](=[O:27])[N:22]([CH3:21])[C:23]1=[O:28]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 70261N-MethylmaleimideHCID 68929363HCID 68929363, compound

Product 1

HCID 68448192HCID 68448192, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 962WaterSolvent

Procedure

To an oven dried, argon purged flask fitted with magnetic stir-bar is charged 5-bromo-1-(tert-butyldimethylsilyl)-1H-indol-3-ylboronic acid 15 (141.6 mg, 0.400 mmol), N-Methyl maleimide 16 (22.2 mg, 0.200 mmol), Rhodium catalyst (0.05 equiv.), anhydrous dioxane (1 mL) and stirring begun. H2O (0.05 mL) added, and mixture heated in an oil bath as per the conditions outlined in Table 9 below. The reaction mixture was filtered through silica gel bed, and the solvent was evaporated to obtain crude product. The crude product was purified via chromatography on silica gel (20% Ethylacetate/80% Hexanes) to yield 3-(5-bromo-1-(tert-butyldimethylsilyl)-1H-indol-3-yl)-1-methylpyrrolidine-2,5-dione 17. The enantiomeric excess was determined with chiral HPLC.

Workup

  1. customTo an oven dried
  2. customargon purged flask fitted with magnetic stir-bar
  3. temperaturemixture heated in an oil bath as per the conditions
  4. filtrationThe reaction mixture was filtered through silica gel bed
  5. customthe solvent was evaporated
  6. customto obtain crude product
  7. customThe crude product was purified via chromatography on silica gel (20% Ethylacetate/80% Hexanes)

Sources & evidence

ORD record
ord-19e1e9b045614e76a19913dff964634a
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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