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Methanol → N-Cyclopropyl-3-fluoro-5-(4-formyl-2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

HRID 906402
ノート
印刷プレビュー

反応式

HRID 906402 の反応式
C([O:4][CH2:5][C:6]([CH3:23])([CH3:22])[CH2:7][N:8]1[CH:17]=[C:16]([CH:18]=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[C:9]1=[O:21])(=O)C.[CH:24]1([NH:27][C:28](=[O:46])[C:29]2[CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[C:32]([CH3:44])=[C:31]([F:45])[CH:30]=2)[CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].CO>CN(C=O)C.O>[CH:24]1([NH:27][C:28](=[O:46])[C:29]2[CH:34]=[C:33]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[C:9](=[O:21])[N:8]([CH2:7][C:6]([CH3:22])([CH3:23])[CH2:5][OH:4])[CH:17]=[C:16]4[CH:18]=[O:19])[C:32]([CH3:44])=[C:31]([F:45])[CH:30]=2)[CH2:25][CH2:26]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 21914563N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 866409623-(6-Bromo-4-formyl-1-oxoisoquinolin-2(1H)-yl)-2,2-dimethylpropyl acetate

生成物 1

HCID 86640963N-Cyclopropyl-3-fluoro-5-(4-formyl-2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide
収率 101.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A solution of 3-(6-bromo-4-formyl-1-oxoisoquinolin-2(1H)-yl)-2,2-dimethylpropyl acetate (Example 1e, 0.25 g) in DMF (10 mL) was treated with N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.28 g), Pd-118 (0.024 g) and potassium carbonate (0.31 g) under nitrogen. The resulting mixture was stirred at 70° C. for 6 h. Methanol (10 mL) was added and stirred at room temperature for 1 h. The reaction mixture was diluted with water (250 mL), and extracted with ethyl acetate (300 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified (SiO2 chromatography, elution with 100% ethyl acetate) to afford the subtitle compound (0.30 g) as an oil.

後処理

  1. stirringstirred at room temperature for 1 h
  2. extractionextracted with ethyl acetate (300 mL)
  3. dry with materialThe organic was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product
  7. customThe crude product was purified
  8. wash(SiO2 chromatography, elution with 100% ethyl acetate)

出典と根拠

ORDレコード
ord-7d92c12ce7344c58967dd8ffdf1a24cf
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012980B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート