Trimethylsilylacetylene → 4-Ethynylcinnoline

HRID 1255942Notes

Reaction equation

HRID 1255942 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1.[C:12]([Si](C)(C)C)#[CH:13]>CO>[C:12]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1)#[CH:13]

Participants

4

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 577752184-Bromocinnoline

Product 1

HCID 577751514-Ethynylcinnoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound can be synthesized from 4-ethynylcinnoline and N-(3-cyclopropyl-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3-iodo-4-methylbenzamide in a manner similar to that described for Example 1 (nitro reduction performed in a manner similar to that described for Example 10; 0.25M in MeOH/10% AcOH). 4-ethynylcinnoline is prepared from 4-bromocinnoline and ethynyltrimethylsilane according to the 2 steps procedure described in Example 1.

Sources & evidence

ORD record
ord-860136d3e644491f981dab7d679d053c
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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