2-(Tributylstannyl)pyridine → HCID 18917533, compound

HRID 1735262Notes

Reaction equation

HRID 1735262 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4Br)=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[Sn](CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=4)=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 18917534HCID 18917534, compound

Product 1

HCID 18917533HCID 18917533, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.94 g of N-[4-(5H-pyrrolo-[2, 1-c][1,4]benzodiazepin-10(11H) -ylcarbonyl)phenyl]-2-bromobenzamide, 2.95 g of 2-pyridyl tri-n-butyl tin and 400 mg of tetrakis (triphenylphosphine)palladium(O) is refluxed for 24 hours in degassed toluene for 24 hours. The reaction mixture is concentrated in vacuo to a residue which is purified by column chromatography on silica gel by elution with 70% ethyl acetate:hexane to give 900 mg of the desired product as a pale yellow solid:M+ 1=485.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to a residue which
  2. customis purified by column chromatography on silica gel by elution with 70% ethyl acetate

Sources & evidence

ORD record
ord-92204932077d4668bdebff87e5ce82f0
Source dataset
uspto-grants-1996_07
Patent number
US05536718

Reaction notes

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