Cesium carbonate → 3-(3-Bromo-5-chlorophenoxy)-4-methylpyridine-2-carbonitrile

HRID 505560

反応式

HRID 505560 の反応式
F[C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[Br:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([Cl:18])[CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:11][C:12]1[CH:13]=[C:14]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:19][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 184233522-Pyridinecarbonitrile,3-fluoro-4-methyl-(9CI)HCID 226301803-Bromo-5-chlorophenol

生成物 1

HCID 684280523-(3-Bromo-5-chlorophenoxy)-4-methylpyridine-2-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 3-fluoro-4-methylpyridine-2-carbonitrile (2.1 g, 15.43 mmol), 3-bromo-5-chlorophenol (3.68 g, 17.74 mmol) and cesium carbonate (5.03 g, 15.43 mmol) in DMF (30 mL) was heated at 70° C. for 1 hour and then at 80° C. for another hour, after which the mixture was partitioned between water (300 mL) and ethyl acetate (2×500 mL). The combined extracts were washed with water (100 mL) and then brine (100 mL), dried over MgSO4, filtered, and the solvent removed in vacuo. The residue was chromatographed using RediSep column (330 g) and eluted with a gradient of 0-10% EtOAc/CH2Cl2 and the pure fractions combined and concentrated on the rotary evaporator to give the title compound. LRMS (M+1)=324.9.

後処理

  1. waitat 80° C. for another hour
  2. customafter which the mixture was partitioned between water (300 mL) and ethyl acetate (2×500 mL)
  3. washThe combined extracts were washed with water (100 mL)
  4. dry with materialbrine (100 mL), dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was chromatographed
  8. washeluted with a gradient of 0-10% EtOAc/CH2Cl2
  9. concentrationconcentrated on the rotary evaporator

出典と根拠

ORDレコード
ord-6245e0afc08d43e5a1d79d59a358a21a
出典データセット
uspto-grants-2010_08
特許番号
US07781454B2

関連ノート

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