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1-(1-Ethylpiperazin-4-yl)-3-bromoisoquinoline → 1-(4-Ethylpiperazin-1-yl)-3-(2-ethoxycarbonylindan-5-yl)isoquinoline

HRID 1251252
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인쇄 미리보기

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HRID 1251252 반응식
[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Sn](CCCC)(CCCC)CCCC)[CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].Br[C:29]1[N:30]=[C:31]([N:39]2[CH2:44][CH2:43][N:42]([CH2:45][CH3:46])[CH2:41][CH2:40]2)[C:32]2[C:37]([CH:38]=1)=[CH:36][CH:35]=[CH:34][CH:33]=2>C1(C)C(C)=CC=CC=1.C(OCC)(=O)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>[CH2:45]([N:42]1[CH2:41][CH2:40][N:39]([C:31]2[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:38]=[C:29]([C:11]3[CH:12]=[C:13]4[C:8](=[CH:9][CH:10]=3)[CH2:7][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:14]4)[N:30]=2)[CH2:44][CH2:43]1)[CH3:46]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 225034712-Ethoxycarbonyl-5-(tributylstannyl)indane

생성물 1

HCID 225026151-(4-Ethylpiperazin-1-yl)-3-(2-ethoxycarbonylindan-5-yl)isoquinoline수율 90.8%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 7237
O-Xylene
용매
HCID 8857Ethyl Acetate용매

실험 절차

2-Ethoxycarbonyl-5-(Tributylstannyl)indane (3.04 g) and 3-bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (0.87 g) were heated under reflux overnight in the presence of tetrakistriphenylphosphinepalladium(0) (0.12 g) in xylene in nitrogen atmosphere. After cooling, the reaction solution was diluted with ethyl acetate and filtered. The filtrate was extracted with 2N hydrochloric acid, and the resulting aqueous layer was washed with ethyl acetate, adjusted to pH 10 with a 8N aqueous solution of sodium hydroxide, and then extracted with ethyl acetate. The extract was washed with a 10% aqueous solution of sodium carbonate and brine, and dried over magnesium sulfate. The solvent was evaporated, to give 1-(4-ethylpiperazin-1-yl)-3-(2-ethoxycarbonylindan-5-yl)isoquinoline (1.06 g) as a brown viscous oil.

후처리

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with 2N hydrochloric acid
  4. washthe resulting aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a 10% aqueous solution of sodium carbonate and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-de42535068f34bdc8645a4f8a14b4d3c
출처 데이터셋
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06340759B1

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