HCID 12628585, 화합물 → Ethyl 3-methyl-1H-indole-5-carboxylate

HRID 2085550노트

반응식

HRID 2085550 반응식
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]

참가 물질

5

반응물 1

HCID 12628585HCID 12628585, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-9f18917448df481b93bfa5a8b3971278
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06720433B2

반응 노트

불러오는 중…