Sodium hydride → HCID 86648959、化合物

HRID 449918

反応式

HRID 449918 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4](Cl)=[O:5].[H-].[Na+].[Br:15][C:16]1[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][N:17]=1>CN(C=O)C.C(OCC)(=O)C>[Br:15][C:16]1[CH:21]=[C:20]([NH:22][C:4](=[O:5])[C:3]2[C:2]([Cl:1])=[CH:10][C:9]([I:11])=[CH:8][C:7]=2[Cl:12])[CH:19]=[CH:18][N:17]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 3464554-Amino-2-bromopyridineHCID 866489582,6-Dichloro-4-iodobenzoyl chloride

生成物 1

HCID 86648959HCID 86648959、化合物収率 40.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

To a cooled (0° C.) solution of 2,6-dichloro-4-iodobenzoyl chloride (70 mg, 0.21 mmol) in DMF (2 mL) was added NaH (17 mg, 0.42 mmol). The mixture was stirred for 10 minutes and then 2-bromopyridin-4-amine (40 mg, 0.23 mmol) was added. The resulting mixture was slowly warmed to 25° C., diluted with ethyl acetate (10 mL), quenched with water (1 mL), washed with saturated Na2CO3 and water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel chromatography (Pet Ether/EtOAc=20:1 to 3:1) to afford N-(2-bromopyridin-4-yl)-2,6-dichloro-4-iodobenzamide (40 mg, 40% yield). LCMS (ESI) m/z: 470.9 [M+H+].

後処理

  1. customquenched with water (1 mL)
  2. washwashed with saturated Na2CO3 and water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel chromatography (Pet Ether/EtOAc=20:1 to 3:1)

出典と根拠

ORDレコード
ord-ddc5ea3b64ed4938a33ec0ef9afda5ed
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

関連ノート

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