Cesium carbonate → methyl 3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoate

HRID 1454957ノート

反応式

HRID 1454957 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:24])[C:11]=2[C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[C:15]([O:17][CH3:18])=[O:16])[N:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[OH:39]>CN1C(=O)CCC1>[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[O:39][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:24])[C:11]=2[C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[C:15]([O:17][CH3:18])=[O:16])[N:7]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 57531227methyl 3-(2-chloro-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoate

生成物 1

HCID 57531245methyl 3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoate

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

To a solution of methyl 3-(2-chloro-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoate (1.05 g, 3.05 mmol) and Cs2CO3 (2.97 g, 9.15 mmol) dissolved in NMP (20 mL) was added 2,4 difluoro phenol (475 mg, 3.66 mmol). The mixture was heated to 80° C. for 1 hr until the reaction was complete via LCMS analysis. The reaction was poured into 500 mL of ice/H2O and the solid precipitate was collected. The crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH) to yield the title compound.

後処理

  1. customthe solid precipitate was collected
  2. customThe crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH)

出典と根拠

ORDレコード
ord-0ce05da8e0d7418d92f6486c5635e4d1
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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