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Pyruvic Acid → 6-Chloro-1H-indole-2-carboxylic acid

HRID 1466910
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HRID 1466910 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:8]=1)[NH2:7].[C:10]([OH:15])(=[O:14])[C:11]([CH3:13])=O.C1N2CCN(CC2)C1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:8]=[C:6]2[C:5]([CH:13]=[C:11]([C:10]([OH:15])=[O:14])[NH:7]2)=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 6396975-Chloro-2-iodoaniline

생성물 1

HCID 855846-Chloro-1H-indole-2-carboxylic acid

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

5-Chloro-2-iodoaniline (5.8 g, 23 mmol) and pyruvic acid (8 mL, 115 mmol) were dissolved in DMF (100 mL). DABCO (12.8 g, 115 mmol) was added and N2 (g) was bubbled through solution for 20 minutes, then palladium acetate (1.03 g, 4.6 mmol) was added. The reaction was heated to 110° C. for 1 hour then submitted to aqueous workup and purified by silica gel chromatography (0-100% EtOAc in hexanes) to yield the title compound.

후처리

  1. customN2 (g) was bubbled through solution for 20 minutes
  2. custompurified by silica gel chromatography (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-3c37bce5ab274f138cbbbc2e7c60824b
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000025B2

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