3,5-Bis(trifluoromethyl)benzoyl chloride → N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 877999ノート

反応式

HRID 877999 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH3:9].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:20][C:21]([F:36])([F:35])[C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:25](Cl)=[O:26]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:9])[C:25](=[O:26])[C:24]1[CH:23]=[C:22]([C:21]([F:36])([F:35])[F:20])[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=1

参加物

5

反応物 3

HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 680039054-bromo-N-methylpyridin-3-amine

生成物 1

HCID 86670692N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of (4-bromo-pyridin-3-yl)-methyl-amine (1 g, 5.376 mmol) in THF (8 mL) was added LiHMDS (1M solution in THF, 10.7 mL, 10.7 mmol, CAS RN 4039-32-1) dropwise at −78° C., and stirred for 15 minutes before 3,5-bis-trifluoromethyl-benzoyl chloride (1.5 mL, 8.06 mmol, CAS RN 785-56-8) was added to the reaction mixture. After stirring at −78° C. for 1 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (10 mL) and diluted with EtOAc (40 mL). The combined organic layers were washed with brine (15 mL), dried over anhydrous Na2SO4, filtered, and evaporated off in vacuo. The residue was purified by column chromatography over silica gel (15% EtOAc in n-hexane) to afford the title compound. Pale yellow solid (985 mg, 43%). MS (ESI): m/z=427.2 [M+H]+.

後処理

  1. additionwas added to the reaction mixture
  2. customwas quenched with saturated aqueous NH4Cl solution (10 mL)
  3. additiondiluted with EtOAc (40 mL)
  4. washThe combined organic layers were washed with brine (15 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated off in vacuo
  8. customThe residue was purified by column chromatography over silica gel (15% EtOAc in n-hexane)

出典と根拠

ORDレコード
ord-c62f8483bb5a462889152995cac312b1
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

反応ノート

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