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 931390Notes

Reaction equation

HRID 931390 reaction equation
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

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547Azobisisobutyronitrile2×HCID 90050549N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)-N-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-b]pyridine-2-carboxamide

Product 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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ca1c5bc5e49f47e0847dd8b09e0d7930
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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