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

HRID 1454956ノート

反応式

HRID 1454956 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-783b021d3b6844889fdff97ae2fd17d9
出典データセット
uspto-grants-2009_01
特許番号
US07482345B2

反応ノート

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