Dimethylformamide → Methyl 2-cyano-6-methylisonicotinate

HRID 571872

반응식

HRID 571872 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:14]

참가 물질

4

반응물 2

HCID 6228DimethylformamideHCID 2759833Methyl 2-Chloro-6-methylisonicotinate

생성물 1

HCID 58802283Methyl 2-cyano-6-methylisonicotinate

시약·촉매·용매 1

HCID 11186Zinc cyanide (Zn(CN)2)촉매

반응 조건

온도
160 °C

실험 절차

Under N2, methyl 2-chloro-6-methylisonicotinate (CAS 3998-90-1) (1.000 g, 5.39 mmol, Eq: 1.00), zinc cyanide (759 mg, 6.47 mmol, Eq: 1.2) and Tetrakis-triphenylphosphin-palladium (623 mg, 539 μmol, Eq: 0.1) were mixed in DMF (17 ml). The RM was stirred under microwave at 160° C. for 30 minutes. Control with TLC: the reaction was finished. The RM was partitioned between EtOAc and water; extracted; the organic phase was dried over MgSO4; filtered; concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, 5% to 30% EtOAc in heptane). Purple solid. MS (ISP): 177.2 ([M+H]+)

후처리

  1. customThe RM was partitioned between EtOAc and water
  2. extractionextracted
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 100 g, 5% to 30% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-8aad0ea1d32840aab9b9837366dd4171
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029370B2

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