Hydrochloric Acid → HCID 67189430, compound

HRID 1695211Notes

Reaction equation

[CH3:1][C:2]#[N:3].C([Li])CCC.C[O:10][C:11]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:17]=[CH:16]2)=O.Cl>C1(C)C=CC=CC=1.CCCCCC>[O:10]=[C:11]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([Si:22]([CH:26]([CH3:28])[CH3:27])([CH:29]([CH3:31])[CH3:30])[CH:23]([CH3:24])[CH3:25])[CH:17]=[CH:16]2)[CH2:1][C:2]#[N:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 393 μL of anhydrous CH3CN (7.5 mmol) in 6 mL of dry toluene cooled down to −78° C., 5.35 mL of butyllithium in hexane solution (1.6 N) were added dropwise. The mixture was left stirring at −78° C. for 20 minutes and then a solution of 500 mg of 1-triisopropylsilanyl-1H-indole-5-carboxylic acid methyl ester (1.5 mmol) in 2 mL of dry toluene were added and the reaction allowed to reach room temperature. Upon reaction completion after about 20 minutes the mixture was cooled down to 0° C. and HCl 2N was added to pH 2. The organic phase was separated, dried over Na2SO4 and concentrated under reduced pressure, affording 490 mg of title product which was used in the next step without further purification (yield=96%).

Workup

waitThe mixture was left
customto reach room temperature
customUpon reaction completion after about 20 minutes the mixture
temperaturewas cooled down to 0° C.
customThe organic phase was separated
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c42a0efc14554a8bbb35d072ac169545
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163729B2

Reaction notes

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