Trifluoroacetic acid → HCID 67067426, compound

HRID 1261791Notes

Reaction equation

HRID 1261791 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[NH:5][CH:6]([CH3:31])[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([C:18]#[N:19])[CH:17]=1)[N:14]([CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:13][CH2:12]2)=O)[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:32])[NH:5][CH:6]([CH3:31])[CH2:7][C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([C:18]#[N:19])[CH:17]=1)[N:14]([CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH2:13][CH2:12]2)[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67067481HCID 67067481, compound

Product 1

HCID 67067426HCID 67067426, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of (2-{1-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-7-cyano-2,3-dihydro-1H-indol-5-yl}-1-methyl-2-oxo-ethyl)-carbamic acid ethyl ester (IV) (10 g, 0.02 mole), toluene (80 ml), triethyl silyl hydride (5.57 g, 0.04 mol) and trifluoroacetic acid (1.36 g, 0.01 mole), was stirred at 25-30° C. for a period of 6 hours. The reaction mass was quenched with water (50 ml) and toluene layer was dried over sodium sulphate. The solvent was evaporated under reduced to give 6.7 g of (V) as oil.

Workup

  1. customThe reaction mass was quenched with water (50 ml) and toluene layer
  2. dry with materialwas dried over sodium sulphate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4d05df578bee41a4841835477030bb56
Source dataset
uspto-grants-2013_06
Patent number
US08471039B2

Reaction notes

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