Sodium hydride → 7-bromo-6-fluoro-2-(4-methoxybenzyl)isoquinolin-1(2H)-one

HRID 1913123ノート

反応式

HRID 1913123 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[F:13].[H-].[Na+].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CC(N(C)C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:22][C:21]3[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[C:9]2=[O:12])=[CH:4][C:3]=1[F:13]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 598182537-Bromo-6-fluoro-1,2-dihydroisoquinolin-1-one

生成物 1

HCID 598182577-bromo-6-fluoro-2-(4-methoxybenzyl)isoquinolin-1(2H)-one収率 116.3%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

実験手順

9.66 g (39.9 mmol) of 7-Bbromo-6-fluoro-2H-isoquinolin-1-one (95) were dissolved in 180 ml of dimethyl acetamide and 1.92 g (48.0 mmol) of sodium hydride (60%) were added. After 1 h at room temperature a solution of 7.50 g (48.0 mmol) of 4-methoxy benzylchloride in 25 ml of dimethyl acetamide was added. The mixture was stirred at room temperature until complete conversion was achieved. The solvent was removed under reduced pressure, the residue was taken up in saturated sodium bicarbonate solution and extracted three times with dichloromethane. The organic layers were dried with magnesium sulfate and evaporated to yield 16.8 g of a dark oil as crude product, which was stirred in methanol. Filtration of the precipitate gave 6.56 g of the title compound as a yellow solid. The mother liquor was evaporated and the residue purified by preparative HPLC to yield additional 2.62 g of the desired product. Rt=1.71 min (Method C). Detected mass: 362.3/364.3 (M+H+).

後処理

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe organic layers were dried with magnesium sulfate
  4. customevaporated

出典と根拠

ORDレコード
ord-3946d9c3b6e64458b4193941bfbdb2d4
出典データセット
uspto-grants-2013_12
特許番号
US08609691B2

反応ノート

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