Tributylstannane → 5-(((4-Methoxybenzyl)oxy)methyl)-1'-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 931390노트

반응식

HRID 931390 반응식
C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C.Br[C:27]1[C:28]([N:33]([CH2:56][O:57][CH2:58][CH2:59][Si:60]([CH3:63])([CH3:62])[CH3:61])[C:34]([C:36]2[O:55][C:39]3=[N:40][CH:41]=[C:42]([CH2:44][O:45][CH2:46][C:47]4[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=4)[CH:43]=[C:38]3[CH:37]=2)=[O:35])=[N:29][CH:30]=[CH:31][CH:32]=1>C1C=CC=CC=1>[CH3:54][O:53][C:50]1[CH:51]=[CH:52][C:47]([CH2:46][O:45][CH2:44][C:42]2[CH:43]=[C:38]3[CH2:37][C:36]4([C:27]5[C:28](=[N:29][CH:30]=[CH:31][CH:32]=5)[N:33]([CH2:56][O:57][CH2:58][CH2:59][Si:60]([CH3:63])([CH3:62])[CH3:61])[C:34]4=[O:35])[O:55][C:39]3=[N:40][CH:41]=2)=[CH:48][CH:49]=1

참가 물질

5

반응물 3

HCID 5948TributylstannaneHCID 6547Azobisisobutyronitrile2회HCID 90050549N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)-N-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-b]pyridine-2-carboxamide

생성물 1

HCID 900505505-(((4-Methoxybenzyl)oxy)methyl)-1'-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

A deoxygenated solution of tributyltin hydride (0.779 g, 2.68 mmol) and AIBN (43 mg, 0.26 mmol) in benzene (44 mL) was added dropwise over 2 h to a deoxygenated solution of N-(3-bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)-N-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-b]pyridine-2-carboxamide (0.80 g, 1.3 mmol) and AIBN (87 mg, 0.53 mmol) in benzene (86 mL) at reflux, and the heating was continued for 1 h. The excess tributyl tinhydride was quenched with thiophenol (0.5 mL) and the reaction mixture was concentrated. The residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in petroleum ether to give the title compound as a racemic mixture. MS: m/z=520.2 (M+1).

후처리

  1. temperatureat reflux
  2. customThe excess tributyl tinhydride was quenched with thiophenol (0.5 mL)
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-ca1c5bc5e49f47e0847dd8b09e0d7930
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296750B2

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