Cesium carbonate → 6-Bromo-1-(3-fluorobenzyl)indoline

HRID 871073

反応式

HRID 871073 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][CH:3]=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 680073-Fluorobenzyl bromideHCID 130983796-Bromo-2,3-dihydro-1H-indole

生成物 1

HCID 904086526-Bromo-1-(3-fluorobenzyl)indoline

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

A mixture of 6-bromoindoline (750 mg, 3.79 mmol), 1-(bromomethyl)-3-fluorobenzene (697 pt, 5.68 mmol) and cesium carbonate (1.851 g, 5.68 mmol) in N,N-dimethylformamide (7.573 mL) was stirred at 110° C. for 2 hours. The mixture was cooled, diluted with 100 mL ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco®, Redi-Sep® column), eluting with a gradient of 2-50% ethyl acetate/hexane, afforded the title compound. LCMS: 306 (M+H)+.

後処理

  1. temperatureThe mixture was cooled
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel flash chromatography (Isco®, Redi-Sep® column)
  7. washeluting with a gradient of 2-50% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-88a32b9c0dec4ded89645f7fd044b689
出典データセット
uspto-grants-2015_03
特許番号
US08969375B2

関連ノート

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