Tetrabutylammonium Fluoride → HCID 22714298, compound

HRID 351753Notes

Reaction equation

HRID 351753 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][N:21]=3)[C:16](=[O:23])[C:15]([C:24]([NH2:26])=[O:25])=[CH:14]2)[CH:10]=[CH:11][CH:12]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:6]([C:7]1[CH:8]=[C:9]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][N:21]=3)[C:16](=[O:23])[C:15]([C:24]([NH2:26])=[O:25])=[CH:14]2)[CH:10]=[CH:11][CH:12]=1)#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22714305HCID 22714305, compound

Product 1

HCID 22714298HCID 22714298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[3-(trimethylsilylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Step 2 in THF (30 mL/mmol) at 0° C. was added 1M tetrabutylammonium fluoride in THF (1.5 eq) and the resulting mixture was stirred at 0° C. for 30 minutes. The mixture was partitioned between methylene chloride and water and the organic phase was dried and evaporated. The crude 1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin4-one-3-carboxamide product was used as such in the next step.

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. customthe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-1e8f845a209c49f2b4e5fd270c1e99ca
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

Loading…