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

HRID 717816노트

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HRID 717816 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4503de346bc442439c003d275e7187d6
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193721B2

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