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

HRID 1952349ノート

反応式

HRID 1952349 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 184233523-Fluoro-4-methylpyridine-2-carbonitrileHCID 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 (11-1; 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 to 70° C. for 1 hour and then to 80° C. for 1 hour. After this time, the reaction 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 a 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. customAfter this time, the reaction mixture was partitioned between water (300 mL) and ethyl acetate (2×500 mL)
  2. washThe combined extracts were washed with water (100 mL)
  3. dry with materialbrine (100 mL), dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue was chromatographed
  7. washeluted with a gradient of 0-10% EtOAc/CH2Cl2
  8. concentrationconcentrated on the rotary evaporator

出典と根拠

ORDレコード
ord-d16274119f9545c7adfe95a1925576e3
出典データセット
uspto-grants-2013_03
特許番号
US08404856B2

反応ノート

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