Sodium hydride → HCID 57808168、化合物

HRID 730315

反応式

HRID 730315 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:18]=[CH:17][N:16]=1>CN(C=O)C>[F:30][C:27]([F:28])([F:29])[C:24]1[CH:23]=[CH:22][C:21]([C:19]2[CH:20]=[CH:15][N:16]=[C:17]([O:1][C:2]3[CH:11]=[C:10]4[C:5]([CH:6]=[CH:7][CH:8]=[N:9]4)=[CH:4][CH:3]=3)[CH:18]=2)=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridineHCID 1354268667-Hydroxyquinoline

生成物 1

HCID 57808168HCID 57808168、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
155 °C

実験手順

To an oven-dried, 50-mL, round-bottomed flask were added 7-hydroxyquinoline (Aldrich) (87 mg, 0.6 mmol) and DMF (1 mL). The solution was place under nitrogen, and NaH (24 mg, 0.6 mmol) was added in one portion. After stirring for 10 min, 2-chloro-4-(4-trifluoromethylphenyl) pyridine (Example 410 (c), 129 mg, 0.5 mmol) was added. The reaction mixture was heated in a 155° C. oil bath for 72 h. After cooling to room temperature, the reaction mixture was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, concentrated in vacuo. The crude material was purified on a Biotage 40 S column (3:1 hexanes:EtOAc) to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 367 (M+1). Mp: 156.5-158.5° C.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between EtOAc and brine
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified on a Biotage 40 S column (3:1 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-3d611c09c1ea4d0fa4d46beb656e165e
出典データセット
uspto-grants-2009_09
特許番号
US07582657B2

関連ノート

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