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Lithium Chloride → Ethyl N-(3,4-dichlorobenzyl)-4-(2-pyridyl)indole-2-carboxylate

HRID 2305584
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HRID 2305584 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1.C([Sn](CCCC)(CCCC)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)CCC.[Cl-].[Li+]>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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[CH2:11][N:6]1[C:7]2[C:3](=[C:2]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[CH:10]=[CH:9][CH:8]=2)[CH:4]=[C:5]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 22311024Ethyl 4-bromo-N-(3,4-dichlorobenzyl)indole-2-carboxylate

생성물 1

HCID 22311015Ethyl N-(3,4-dichlorobenzyl)-4-(2-pyridyl)indole-2-carboxylate수율 54%

시약·촉매·용매 1

HCID 178527695
HCID 178527695, 화합물
촉매

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온도
105 °C

실험 절차

Ethyl 4-bromo-N-(3,4-dichlorobenzyl)indole-2-carboxylate (0.15 g), 2-(tri-n-butylstannyl) pyridine (0.155 g), lithium chloride (30 mg) and tetrakis triphenylphosphine-palladium(0) (15 mg) were dissolved in anhydrous degassed toluene under argon and warmed at 105° C. for 16 hours. The reaction was then cooled to room temperature and partitioned between water and dichloromethane. Combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using i-hexane-30% ethyl acetate as eluent to give the desired end product as a white solid (0.08 g, 54%); M/z (+) 425 (M+).

후처리

  1. customin anhydrous degassed toluene under argon
  2. temperatureThe reaction was then cooled to room temperature
  3. custompartitioned between water and dichloromethane
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-092aacb44c1f45e4b59ad6d40a9a6575
출처 데이터셋
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06441004B1

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