2-(Tributylstannyl)pyridine → HCID 18917533, compound

HRID 1290966Notes

Reaction equation

HRID 1290966 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[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

5

Reactant 2

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

Product 1

HCID 18917533HCID 18917533, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 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-eb421ebfef8f4d8e8d4897d13b11ae1a
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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