Diisopropylethylamine → HCID 67994864, compound

HRID 2361319Notes

Reaction equation

HRID 2361319 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:10])[CH:8]=2)[CH:3]=[CH:2]1.CCN(C(C)C)C(C)C.[C:20](=O)([O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[O:21]N1C(=O)CCC1=O>O1CCOCC1.CCOC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:20](=[O:21])[O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2560966-AminoindoleHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate

Product 1

HCID 67994864HCID 67994864, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a yellow, homogeneous solution of 1H-indol-6-amine (1.3007 g, 9.84 mmol) and DIPEA (2.58 mL, 14.76 mmol) in 1,4-dioxane (19.68 mL) under nitrogen was added 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate (2.81 g, 10.83 mmol) The reaction was stirred overnight, diluted with EtOAc (1500 mL), washed with water (3×50 mL) and brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo to give the desired product (2.666 g, 9.65 mmol, 98% yield) as a light tan solid.

Workup

  1. washwashed with water (3×50 mL) and brine (50 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79781d4f14134778a2c2c9bfb185fec4
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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