Triethylamine → Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate

HRID 717816ノート

反応式

HRID 717816 の反応式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:20]([N:22](CC)CC)C.C[Si](C#N)(C)C>C(#N)C>[Cl:1][C:2]1[C:3]([C:20]#[N:22])=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 66993068Methyl 5-chloro-2-(3-fluorophenyl)nicotinate 1-oxide

生成物 1

HCID 58515932Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate収率 92.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

Methyl 5-chloro-2-(3-fluorophenyl)nicotinate 1-oxide (2.9 g, 10 mmol) was stirred in acetonitrile (30 mL) with triethylamine (2.2 mL, 16 mmol) and trimethylsilyl cyanide (3.4 mL, 26 mmol) was added. The mixture was heated at 70° C. for 1 hour. Evaporation and purification by flash column chromatography using ethyl acetate in hexanes (0-20%) gave the desired compound (2.7 g, 90%). LCMS calculated for C14H9ClFN2O2 (M+H)+: m/z=291.1. found: 290.8.

後処理

  1. additionwas added
  2. customEvaporation and purification by flash column chromatography

出典と根拠

ORDレコード
ord-4503de346bc442439c003d275e7187d6
出典データセット
uspto-grants-2015_11
特許番号
US09193721B2

反応ノート

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