Tetrabutylammonium Fluoride → methyl 3-(2-chloro-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoate

HRID 1454956Notes

Reaction equation

HRID 1454956 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[C:20]([O:22][CH3:23])=[O:21])[C:9](=[O:16])[C:10]#[C:11][Si](C)(C)C)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O.CCOC(C)=O.CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:11]=[CH:10][C:9](=[O:16])[C:8]=2[C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[C:20]([O:22][CH3:23])=[O:21])[N:7]=1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57531244Methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-methoxybenzoate

Product 1

HCID 57531227methyl 3-(2-chloro-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4methoxybenzoate (5.58 g, 13.4 mmol) in THF (200 mL) was added TBAF (20.0 mL, 20 mmol) at 0° C. After 10 min the reaction was complete by TLC analysis and diluted with H2O/EtOAc (1/1). The organic layer was washed with H2O, brine, dried over MgSO4 and concentrated to yield an oil. The crude material was dissolved in NMP (25 mL) and heated to 90° C. for 0.5 hr. The completed reaction was poured into 500 mL of ice water and the solid precipitate was collected and dried.

Workup

  1. washThe organic layer was washed with H2O, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto yield an oil
  5. customThe completed reaction
  6. customthe solid precipitate was collected
  7. customdried

Sources & evidence

ORD record
ord-783b021d3b6844889fdff97ae2fd17d9
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

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