HCID 18917497, compound → HCID 18917557, compound

HRID 1290967Notes

Reaction equation

HRID 1290967 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:18]=[CH:19][C:20]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4Br)=[N:21][CH:22]=3)=[O:16])[CH2:6][C:5]=12>C1(C)C=CC=CC=1.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>[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:18]=[CH:19][C:20]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:20]4[CH:19]=[CH:18][CH:17]=[CH:22][N:21]=4)=[N:21][CH:22]=3)=[O:16])[CH2:6][C:5]=12

Participants

4

Reactant 1

HCID 18917497HCID 18917497, compound

Product 1

HCID 18917557HCID 18917557, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 484 mg of N-[5-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)-2-pyridinyl]-2-bromobenzamide, 814 mg of 4-(N,N-dimethyl)anilino-tri-n-butyl stannane and 100 mg of tetrakis(triphenylphosphine)palladium (O) is refluxed 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 ethyl acetate to give 200 mg of the desired product: M+1=528.

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 ethyl acetate

Sources & evidence

ORD record
ord-3ca53843f48a45b4a41da60c13c9d3e1
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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