Pyruvic Acid → HCID 90039786、化合物

HRID 526007ノート

反応式

HRID 526007 の反応式
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.N12CCN(CC1)CC2.[NH2:15][C:16]1[C:25](I)=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:27])[N:17]=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:23][O:22][C:20]([C:19]1[CH:24]=[C:25]2[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[NH:15][C:16]2=[N:17][C:18]=1[CH3:27])=[O:21]

参加物

6

反応物 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 59747893Methyl 6-amino-5-iodo-2-methylnicotinate

生成物 1

HCID 90039786HCID 90039786、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Under argon, pyruvic acid (6.90 ml, 100.1 mmol) and 1,4-diazabicyclo[2.2.2]octane (11.2 g, 100.1 mmol) were added to a solution of methyl 6-amino-5-iodo-2-methylnicotinate (9.00 g, 30.8 mmol) in N,N-dimethylformamide (88 ml), and the flask was evacuated and flushed with argon. Argon was subsequently passed through the solution for 5 min, palladium(II) acetate (0.345 g, 1.54 mmol) was then added and the mixture was heated at 100° C. for 2 h. The cooled solution was filtered through Celite and the dimethylformamide was distilled off. The residue was then taken up in water and acidified with hydrochloric acid, giving a solid (6.3 g, 86% of theory). HPLC-MS: log P=1.26; mass (m/z): 235.0 (M+H)+; 1H-NMR (DMSO) 2.79 (s, 3H), 3.85 (s, 3H), 7.19 (s, 1H), 8.62 (s, 1H), 12.50 (s, 1H).

後処理

  1. customthe flask was evacuated
  2. customflushed with argon
  3. filtrationThe cooled solution was filtered through Celite
  4. distillationthe dimethylformamide was distilled off
  5. customgiving a solid (6.3 g, 86% of theory)

出典と根拠

ORDレコード
ord-9a619e9f2d914363960361d9b17d6462
出典データセット
uspto-grants-2016_05
特許番号
US09345247B2

反応ノート

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