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2-(Tributylstannyl)pyridine → 10,11-Dihydro-10-[4-(2-pyridinyl)benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 1956343
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HRID 1956343 반응식
I[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)CCC>C1(C)C=CC=CC=1.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>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 6077842-(Tributylstannyl)pyridineHCID 15298021HCID 15298021, 화합물

생성물 1

HCID 2240533010,11-Dihydro-10-[4-(2-pyridinyl)benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine수율 81.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
120 °C

실험 절차

To a solution of 2.0 g of 10,11-dihydro-10-(4-iodobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 4.39 g of 2-[(tri-n-butyl)stannyl]pyridine in 30 ml of toluene under nitrogen is added 0.2 g of tetrakis(triphenylphosphine)palladium and the mixture heated to 120° C. for 16 hours. The toluene is evaporated in vacuo and the oily residue diluted with 50 ml of chloroform and washed with water, dried(Na2SO4), filtered through diatomaceous earth and evaporated in vacuo to give a residue which is columned on silica gel by elution with 7:1 to 1:1 ethyl acetate:hexane to give 1.44 g of the desired product as a solid, m.p. 170°-172° C.; M+H=366.1; M+Na=388.1.

후처리

  1. customThe toluene is evaporated in vacuo
  2. additionthe oily residue diluted with 50 ml of chloroform
  3. washwashed with water, dried(Na2SO4)
  4. filtrationfiltered through diatomaceous earth
  5. customevaporated in vacuo
  6. customto give a residue which
  7. washis columned on silica gel by elution with 7:1 to 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-72fc42a5ae0341718aff7c12cc059f96
출처 데이터셋
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05780471

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