Pyruvic Acid → 6-Chloro-5-(ethoxycarbonyl)-1H-indole-2-carboxylic acid

HRID 514243

反応式

HRID 514243 の反応式
[NH2:1][C:2]1[C:12](I)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([Cl:14])[CH:3]=1.[C:15]([OH:20])(=[O:19])[C:16]([CH3:18])=O.N12CCN(CC1)CC2>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:14][C:4]1[CH:3]=[C:2]2[C:12]([CH:18]=[C:16]([C:15]([OH:20])=[O:19])[NH:1]2)=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

参加物

6

反応物 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 58247958Ethyl 4-amino-2-chloro-5-iodobenzoate

生成物 1

HCID 582479336-Chloro-5-(ethoxycarbonyl)-1H-indole-2-carboxylic acid収率 129%

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

A solution of ethyl 4-amino-2-chloro-5-iodobenzoate (1.82 g, 5.59 mmol) in N,N-dimethylformamide (18 ml) under argon was admixed with pyruvic acid (1.27 ml, 18.2 mmol) and 1,4-diazabicyclo[2.2.2]octane, evacuated and flushed with argon. Then argon was passed through the solution for 5 min and then palladium(II) acetate (68 mg, 0.30 mmol) was added and the mixture was heated to 100° C. for 2 h. The cooled solution was filterd through Celite and the filtercake was rinsed with ethyl acetate (100 ml). The filtrate (suspension) was washed with hydrochloric acid (2 M; 2×25 ml) and with water (2×25 ml), dried over sodium sulphate and filtered. The filtrate was concentrated to dryness under reduced pressure and gave a red-brown solid (1.93 g, approx. 51% product), which was used for the next step without further purification.

後処理

  1. customevacuated
  2. customflushed with argon
  3. washthe filtercake was rinsed with ethyl acetate (100 ml)
  4. washThe filtrate (suspension) was washed with hydrochloric acid (2 M; 2×25 ml) and with water (2×25 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-5b69fc19fd3d40b48b7200ad64efd53d
出典データセット
uspto-grants-2015_08
特許番号
US09107411B2

関連ノート

読み込み中…