HCID 12628585、化合物 → Ethyl 3-methyl-1H-indole-5-carboxylate

HRID 2085550ノート

反応式

HRID 2085550 の反応式
Br[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH:8][C:3]=1[NH:4][CH2:5][CH:6]=[CH2:7]>C(#N)C.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.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([C:10]1[CH:11]=[C:2]2[C:3](=[CH:8][CH:9]=1)[NH:4][CH:5]=[C:6]2[CH3:7])([O:14][CH2:15][CH3:16])=[O:13]

参加物

5

反応物 1

HCID 12628585HCID 12628585、化合物

生成物 1

HCID 12628587Ethyl 3-methyl-1H-indole-5-carboxylate収率 73.1%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-bromo-4-carboethoxy-N-allylaniline (J. Org. Chem., 45, 2710(1980)) (650 mg, 2.29 mmol) in acetonitrile (10 ml), tetrakis(triphenylphosphine)palladium(0) (132 mg, 0.114 mmol), palladium (II) acetate (25.7 mg, 0.114 mmol) and TEA (0.413 ml, 2.98 mmol) were added and stirred overnight in a sealed tube at 100° C. After filtering the reaction mixture, the filtrate was evaporated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:2) to give the titled compound (340 mg, 73%).

後処理

  1. filtrationAfter filtering the reaction mixture
  2. customthe filtrate was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-9f18917448df481b93bfa5a8b3971278
出典データセット
uspto-grants-2004_04
特許番号
US06720433B2

反応ノート

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