Potassium Carbonate → HCID 67402517, compound

HRID 1186365Notes

Reaction equation

HRID 1186365 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH:11]=[O:12].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]([Si](C)(C)C)([F:22])[F:21]>CN(C)C=O>[F:19][C:20]([F:22])([F:21])[CH:11]([C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[OH:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2671641-Methylindole-2-carboxaldehydeHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 67402517HCID 67402517, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Reference Example 8-2, by use of 1-methyl-1H-indole-2-carbaldehyde (300 mg, 1.88 mmol) dissolved in N,N-dimethylformamide (4.5 mL), potassium carbonate (52 mg, 0.38 mmol) and (trifluoromethyl)trimethylsilane (0.416 mL, 2.82 mmol), the mixture was stirred and reacted at room temperature for 4 hours. Then, purification by preparative thin-layer chromatography (chloroform/methanol=100/1) was performed to give 2,2,2-trifluoro-1-(1-methyl-1H-indol-2-yl)ethanol (Compound DQ) (339 mg, yield: 79%).

Workup

  1. customreacted at room temperature for 4 hours
  2. customThen, purification by preparative thin-layer chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-6724b7912e094bb48e08f4f01862b74f
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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