HCID 21071400, compound → HCID 21071403, compound

HRID 1666848Notes

Reaction equation

HRID 1666848 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH:13]=[C:12]2[CH2:28][CH2:29][N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40])C1C=CC=CC=1>[Pd].CCOC(C)=O>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([Si:18]([CH:22]([CH3:23])[CH3:24])([CH:19]([CH3:20])[CH3:21])[CH:25]([CH3:27])[CH3:26])[CH:13]=[C:12]2[CH2:28][CH2:29][N:30]1[C:31](=[O:40])[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:38]1=[O:39]

Participants

4

Reactant 1

HCID 21071400HCID 21071400, compound

Product 1

HCID 21071403HCID 21071403, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Combine 2-(2-(5-benzyloxy-1-triisopropylsilanyl-1H-indol-3-yl)ethyl)isoindole-1,3-dione and EtOAc (40 mL) and hydrogenated overnight with 1 g 5% Pd/C at atmospheric pressure. Filter through celite, concentrate to dryness, and chromatograph on silica gel eluting stepwise with a gradient 10% EtOAc in hexanes to 30% EtOAc in hexanes to give the title compound as a solid: FDMS 462 (M+1) Analysis for C27F24N2O3Si H2O: calcd: C, 69.55; H, 7.44; N, 6.01. Found: C, 69.44; H, 7.17; N, 6.00.

Workup

  1. filtrationFilter through celite
  2. concentrationconcentrate to dryness, and chromatograph on silica gel eluting stepwise with a gradient 10% EtOAc in hexanes to 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-fd9065487329474384e7b4e5ab29428e
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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