Pyruvic Acid → 6-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

HRID 751672ノート

反応式

HRID 751672 の反応式
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.[Cl:7][C:8]1[CH:13]=[C:12]([NH2:14])[C:11](I)=[CH:10][N:9]=1.C1N2CCN(CC2)C1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:7][C:8]1[N:9]=[CH:10][C:11]2[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[NH:14][C:12]=2[CH:13]=1

参加物

6

反応物 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 454803662-Chloro-5-iodopyridin-4-amine

生成物 1

HCID 378189746-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

試薬・触媒・溶媒 2

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

反応条件

温度
145 °C

実験手順

Pyruvic acid (0.86 mL, 12.4 mmol) was added to a solution of 2-chloro-5-iodo-pyridin-4-ylamine (Preparation 115, 1.05 mg, 4.13 mmol), palladium acetate (56 mg, 0.25 mmol) and DABCO (1.39 g, 12.4 mmol) in anhydrous DMF (30 ml). The reaction mixture was degassed with argon for 20 min, then heated to 145° C. for 2 h. The solvent was removed in vacuo and the residue taken up in water (200 mL). The suspension was made alkaline (pH 9–10) with dilute NaOH solution (1M) and filtered through Celite. After washing of the filtrate with ethyl acetate (50 mL) and ether (50 mL) the pH was adjusted to 3 with dilute HCl solution (1M). Extraction with ethyl acetate (5×50 mL), drying of the combined extracts (MgSO4) and concentration gave the title compound. δH (d6 DMSO): 7.24 (1H, s), 7.42 (1H, s), 8.80 (1H, s); m/z (ES−)=195.02 [M−H]−; RT=2.36 min.

後処理

  1. customThe reaction mixture was degassed with argon for 20 min
  2. customThe solvent was removed in vacuo
  3. filtrationfiltered through Celite
  4. washAfter washing of the filtrate with ethyl acetate (50 mL) and ether (50 mL) the pH
  5. extractionExtraction with ethyl acetate (5×50 mL)
  6. dry with materialdrying of the combined extracts (MgSO4) and concentration

出典と根拠

ORDレコード
ord-d24d81ee9aaa4d339064af4a684d4e25
出典データセット
uspto-grants-2008_07
特許番号
US07405210B2

反応ノート

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