Triethylamine → HCID 21962261, compound

HRID 988871Notes

Reaction equation

HRID 988871 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9]C(=O)C(F)(F)F.[CH2:16]([OH:20])[CH2:17][C:18]#[CH:19].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:7]=1)[NH:9][C:18]([CH2:17][CH2:16][OH:20])=[CH:19]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 21962318HCID 21962318, compound

Product 1

HCID 21962261HCID 21962261, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

N-(2-Bromo4-chlorophenyl)-2,2,2-trifluoroacetamide(step 1, 1.0 eq) was mixed with 3-butyn-1-ol(2.0 eq), dichlorobis(triphenylphosphine)palladium(lI) (2.5% eq), triethylamine(3.0 eq), Cul(5% eq) in DMF(0.2M) in a sealed vessel under N2 and heated to 120° C. for 4 hours. The reaction mixture was then diluted with ethyl acetate, washed with brine and dried over Na2SO4. Furthermore, evaporate the solvent and the residue was purified by flash column chromatography with 2% MeOH/CH2Cl2 to give the described 2-(5-Chloro-1H-indol-2-yl)ethanol in 67% yield. m/z(M−H)194.09

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customFurthermore, evaporate the solvent
  4. customthe residue was purified by flash column chromatography with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-033466ff561b4f7a8b24702b107cc255
Source dataset
uspto-grants-2003_10
Patent number
US06635771B2

Reaction notes

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