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

HRID 1454956노트

반응식

HRID 1454956 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 13387N-methyl-2-pyrrolidone용매HCID 22728543Water ethylacetate용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-783b021d3b6844889fdff97ae2fd17d9
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482345B2

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