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

HRID 514243

반응식

HRID 514243 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b69fc19fd3d40b48b7200ad64efd53d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107411B2

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