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

HRID 751672노트

반응식

HRID 751672 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
145 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d24d81ee9aaa4d339064af4a684d4e25
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405210B2

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