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

HRID 2249695
ノート
印刷プレビュー

反応式

HRID 2249695 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1382030b41e14a70810f10919f346476
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07314888B1

反応ノート

読み込み中…

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