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Formic Acid → 2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid

HRID 2249695
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HRID 2249695 반응식
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[N:4]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(O)=O.C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:21]([O:20][C:18]([C:3]1[N:4]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:5]2[C:10]([CH:2]=1)=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=2)=[O:19])[CH3:22]
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참가 물질

8

반응물 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 178165173-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid

생성물 1

HCID 178165142-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid수율 50.9%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

In 6 ml of N,N-dimethylformamide are suspended 0.30 g of 3-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid, 0.10 g of tetrakis(triphenylphosphine)palladium(0), 0.24 ml of formic acid and 1.36 ml of triethylamine. The suspension is stirred at 80° C. for 5 hours. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1) to obtain 0.12 g of 2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid as a yellow solid product.

후처리

  1. customthe organic layer is separated
  2. customThe organic layer thus obtained
  3. washis washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-1382030b41e14a70810f10919f346476
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07314888B1

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