Triethylamine → HCID 19102673, compound

HRID 1885876Notes

Reaction equation

HRID 1885876 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([OH:14])=[O:13])[CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[CH2:15](N(CC)CC)C.[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[C:22]1([C:28]#[C:29][C:2]2[CH:3]=[C:4]3[C:9](=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:11]=2)[NH:8][CH2:7][CH2:6][CH2:5]3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 149884641,2,3,4-Tetrahydro-6-iodo-8-quinolinecarboxylic acid

Product 2

HCID 19102673HCID 19102673, compoundHCID 19102674HCID 19102674, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 6-iodo-1,2,3,4-tetrahydroquinoline-8-carboxylate was prepared (quant.) in a similar manner to Example 32 (a) from 6-iodo-1,2,3,4-tetrahydroquinoline-8-carboxylic acid. To a mixture of this ester (2 g), bis-triphenylphosphine palladium dichloride (440 mg) and cuprous iodide (120 mg) in DMF (80 ml) was added triethylamine (7 ml) and phenylacetylene (780 mg). The reaction mixture was stirred at 80° C. for 10 hours and then evaporated. The resulting residue was purified by silica gel column chromatography eluting with ethyl acetate-n-hexane (1:7) to give methyl 6-(2-phenylethynyl)-1,2,3,4-tetrahydroquinoline-8-carboxylate.

Workup

  1. customevaporated
  2. customThe resulting residue was purified by silica gel column chromatography
  3. washeluting with ethyl acetate-n-hexane (1:7)

Sources & evidence

ORD record
ord-ff45728fb3ce44d38446a102d50302c2
Source dataset
uspto-grants-1992_09
Patent number
US05147874

Reaction notes

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