1-methyl-2-(tributylstannyl)-1H-pyrrole → 1-Ethyl-3-[7-(1-methyl-1H-pyrrol-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea

HRID 447011

반응식

HRID 447011 반응식
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15](I)=[CH:14][C:13]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[CH3:23][N:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[Sn](CCCC)(CCCC)CCCC>CN(C=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>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:25]3[N:24]([CH3:23])[CH:28]=[CH:27][CH:26]=3)=[CH:14][C:13]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 27693971-methyl-2-(tributylstannyl)-1H-pyrroleHCID 24864395HCID 24864395, 화합물

생성물 1

HCID 248643971-Ethyl-3-[7-(1-methyl-1H-pyrrol-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To a solution of 1-ethyl-3-(7-iodo-5-pyridin-3-yl-benzothiazol-2-yl)-urea (0.10 g, 0.24 mmol) in DMF (2.0 mL) was added N-methyl-2-tributylstannyl-1H-pyrrole (0.18 g, 0.47 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was degassed for half an hour followed by the addition of tetrakis(triphenylphosphine)palladium(0) (0.027 g, 0.024 mmol). The reaction mixture was again degassed for half an hour and then heated at 120° C. for 20 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), DMF was distilled off, added water and extracted with ethyl acetate (×3). The combined organic layer was dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The crude residue was purified by prep-HPLC to provide the title compound as off white solid (0.005 g, 6.0%).

후처리

  1. customThe reaction mixture was degassed for half an hour
  2. customThe reaction mixture was again degassed for half an hour
  3. customAfter the completion of the reaction (TLC monitoring), DMF
  4. distillationwas distilled off
  5. additionadded water
  6. extractionextracted with ethyl acetate (×3)
  7. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  8. customevaporated to dryness under reduced pressure
  9. customThe crude residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-315927f90ba04e2cbc2ca59b3d26b07e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481544B2

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