Tetrabutylammonium Fluoride → Ethyl 6-ethynyl-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1048885Notes

Reaction equation

HRID 1048885 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18]#[C:19][Si](C)(C)C)=[CH:15][CH:16]=3)[C:11](=[O:24])[C:10]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:9]2)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:18]([C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:9]=[C:10]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:11]2=[O:24])#[CH:19]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735996Ethyl 1-(4-fluorophenyl)-4-oxo-6-((trimethylsilyl)ethynyl)-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 121447848Ethyl 6-ethynyl-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Compound Q (205 mg, 0.5 mmol) in THF (2.5 mL) was added a 1M solution of TBAF in THF (554 μL, 0.55 mmol). After thirty minutes the reaction was concentrated in vacuo. Purification by flash chromatography on silica gel afforded 110 mg (65%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.47 (s, 1H), 8.28 (d, J=1.84 Hz, 1H), 7.77-7.69 (m, 3H), 7.54-7.5 (m, 2H), 6.67 (d, J=8.8 Hz, 1H), 4.22-4.19 (m, 3H), 1.28-1.23 (m, 3H); ES-MS [M+1]+: 336.3.

Workup

  1. concentrationAfter thirty minutes the reaction was concentrated in vacuo
  2. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d3533ca0ea734b95a6a3cbab5557f542
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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