Cesium carbonate → 5-bromo-2-(2-chloropyridin-4-yloxy)-N,N-diethylbenzamide

HRID 1970263ノート

反応式

HRID 1970263 の反応式
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][N:3]=1.[Br:9][C:10]1[CH:11]=[CH:12][C:13]([OH:23])=[C:14]([CH:22]=1)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([O:23][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[C:14]([CH:22]=1)[C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 27827922-Chloro-4-fluoropyridineHCID 242852955-bromo-N,N-diethyl-2-hydroxybenzamide

生成物 1

HCID 592723405-bromo-2-(2-chloropyridin-4-yloxy)-N,N-diethylbenzamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

2-Chloro-4-fluoropyridine (0.242 g, 1.837 mmol) was added to a mixture of 5-bromo-N,N-diethyl-2-hydroxybenzamide (0.500 g, 1.837 mmol) and cesium carbonate (1.197 g, 3.67 mmol) in acetonitrile (10.0 mL). The mixture stirred at 100° C. for 8 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown oil. This oil was purified via column chromatography on silica gel (RediSep 80 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford 5-bromo-2-(2-chloropyridin-4-yloxy)-N,N-diethylbenzamide as a thick, yellow oil. MS m/z=383.0 [M+H]+. Calcd for C16H16BrClN2O2: 382.0.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a brown oil
  9. customThis oil was purified via column chromatography on silica gel (RediSep 80 g column, gradient elution with 0-50% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-360d46d15d2f40c3af7464f922160faa
出典データセット
uspto-grants-2013_04
特許番号
US08426447B2

反応ノート

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