Trifluoroacetic acid → HCID 67551142, compound

HRID 1836637Notes

Reaction equation

HRID 1836637 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[N:21])O)=[O:5])[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl.[OH-].[Na+]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH2:9][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[N:21])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67550417HCID 67550417, compound

Product 1

HCID 67551142HCID 67551142, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of the 2-[(3-cyano-1H-indol-5-yl)-hydroxy-methyl]-cyclopropane-carboxylic acid ethyl ester (1.0 g, 3.5 mmol), dichloromethane (25 ml), and trifluoroacetic acid (5 ml) was cooled to 0° C. and treated with triethylsilane (0.57 g, 5.0 mmol). The solution was stirred for 30 min and then diluted with an additional 50 ml dichloromethane and neutralized with 1 N sodium hydroxide. The organic layer was washed with brine (1×50 ml) and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo to a deep amber oil. Silica gel column chromatography (hexanes, ethyl acetate 1:1) afforded 2-(3-cyano-1H-indol-5-ylmethyl)-cyclopropane-carboxylic acid ethyl ester (0.62 g, 56%) as a light yellow oil. LC-MS: 1.38 min; 269.1 (MH)+.

Workup

  1. washThe organic layer was washed with brine (1×50 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe filtrate was concentrated in vacuo to a deep amber oil

Sources & evidence

ORD record
ord-8c74b475dd6a423e86bc871e13cd4ef4
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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