Sodium hydride → N-(2-Bromopyridin-4-yl)-2,6-dichlorobenzamide

HRID 449862

反応式

HRID 449862 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:13]=1[C:14](Cl)=[O:15]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:14](=[O:15])[C:13]2[C:12]([Cl:11])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:21])[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 783922,6-Dichlorobenzoyl chlorideHCID 3464554-Amino-2-bromopyridine

生成物 1

HCID 75464886N-(2-Bromopyridin-4-yl)-2,6-dichlorobenzamide収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 2-bromopyridin-4-amine (0.74 g, 4.3 mmol) in DMF (5 mL) was added to a cooled (0° C.) mixture of NaH (0.31 g, 7.82 mmol, 60% in mineral oil) in DMF (15 mL). The resulting mixture was stirred for 20 minutes at 0° C. and then a solution of 2,6-dichlorobenzoyl chloride (0.82 g, 3.91 mmol) in DMF (5 mL) was added dropwise. The reaction was stirred at 0° C. for 4 hours and then poured onto ice-water (20 mL). The precipitate was collected and filtrate was extracted by EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The resulting solid was combined with the precipitate to afford N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (1.0 g, Yield: 74%). 1HNMR (DMSO-d6, 400 MHz): δ 11.41 (s, 1H), 8.33 (d, J=5.6 Hz, 1H), 7.99 (d, J=1.6 Hz, 1H), 7.64-7.54 (m, 4H). LCMS (ESI) m/z: 345.0 [M+H+].

後処理

  1. temperaturea cooled
  2. stirringThe reaction was stirred at 0° C. for 4 hours
  3. additionpoured onto ice-water (20 mL)
  4. customThe precipitate was collected
  5. extractionfiltrate was extracted by EtOAc (2×50 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-23932c75a17b430198670046a2ff4d14
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

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