Triethylamine → Ethyl 1-(4-fluorophenyl)-4-oxo-6-((trimethylsilyl)ethynyl)-1,4-dihydroquinoline-3-carboxylate

HRID 1048884Notes

Reaction equation

HRID 1048884 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH:7]=[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]2=[O:24].[CH3:25][Si:26]([C:29]#[CH:30])([CH3:28])[CH3:27].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CN(C=O)C>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:8]2[C:9]3[C:4](=[CH:3][C:2]([C:30]#[C:29][Si:26]([CH3:28])([CH3:27])[CH3:25])=[CH:11][CH:10]=3)[C:5](=[O:24])[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7]2)=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 121447944Ethyl 6-bromo-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 131735996Ethyl 1-(4-fluorophenyl)-4-oxo-6-((trimethylsilyl)ethynyl)-1,4-dihydroquinoline-3-carboxylateYield 44%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Compound D (450 mg, 1.15 mmol), trimethylsilylacetylene (179 μL, 1.27 mmol), PdCl2(PPh3)2 (40.5 mg, 0.058 mmol), CuI (22 mg, 0.12 mmol), triethylamine (321 μL, 2.31 mmol) and DMF (5.8 mL) were added to a microwave vial. The vial was capped and place in a microwave reactor at 150° C. for one hour. The reaction was washed with water and brine and extracted with EtOAc (2×). The organics were combined, dried (MgSO4), and concentrated to dryness. Purification by flash chromatography on silica gel afforded 205 mg (44%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.45 (s, 1H), 8.24 (d, J=1.84 Hz, 1H), 7.76-7.73 (m, 2H), 7.68 (dd, J=8.8 Hz, 1H), 7.52 (t, J=8.64, 8.72 Hz, 2H), 6.93 (d, J=8.8 Hz, 1H), 4.22 (q, J=7.08 Hz, 2H), 1.25 (t, J=7.12, 7.04 Hz, 3H), 0.24 (s, 9H); ES-MS [M+1]+: 408.2.

Workup

  1. customThe vial was capped
  2. washThe reaction was washed with water and brine
  3. extractionextracted with EtOAc (2×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-75c710e59f204ae088a7e4ee1743fa0c
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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