Dimethylformamide → Methyl 2-cyano-6-methylisonicotinate

HRID 571872

反応式

HRID 571872 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 58802283Methyl 2-cyano-6-methylisonicotinate

試薬・触媒・溶媒 1

HCID 11186Zinc cyanide (Zn(CN)2)触媒

反応条件

温度
160 °C

実験手順

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]+)

後処理

  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)

出典と根拠

ORDレコード
ord-8aad0ea1d32840aab9b9837366dd4171
出典データセット
uspto-grants-2015_05
特許番号
US09029370B2

関連ノート

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