2-Chloro-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinoline → {6-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-4-methylquinolin-2-yl} methylamine

HRID 2112816Notes

Reaction equation

HRID 2112816 reaction equation
Cl[C:2]1C=C(C)C2C(=CC=C(C#CC3C=CC(C4C=CC(Cl)=CC=4)=CN=3)C=2)[N:3]=1.Br[C:29]1[CH:38]=[C:37]([CH3:39])[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:40]#[C:41][C:42]3[CH:47]=[CH:46][C:45]([C:48]4[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=4)=[CH:44][N:43]=3)[CH:35]=2)[N:30]=1>CN1C(=O)CCC1.CN(C=O)C>[Cl:54][C:51]1[CH:52]=[CH:53][C:48]([C:45]2[CH:46]=[CH:47][C:42]([C:41]#[C:40][C:34]3[CH:35]=[C:36]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([CH2:2][NH2:3])[CH:38]=[C:37]4[CH3:39])=[N:43][CH:44]=2)=[CH:49][CH:50]=1

Participants

5

Reactant 2

HCID 860798502-Chloro-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinolineHCID 860798522-Bromo-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinoline

Product 1

HCID 69064008{6-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-4-methylquinolin-2-yl} methylamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Analogously to Example 1k, the following Examples may be prepared starting from 2-chloro-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinoline (Example 1h) or 2-bromo-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinoline (Example 1i) and the corresponding amines: Examples 1.8-1.9, 1.11, 1.15-1.21, 1.23 and 1.28 were prepared by heating in NMP in the microwave (300 W, 190° C.; 30-60 min); Example 1.13 was prepared by heating in DMF in the microwave (150 W, 170° C.; 10 min); and Example 1.51 was obtained as a by-product.

Workup

  1. customExample 1.13 was prepared
  2. customand Example 1.51 was obtained as a by-product

Sources & evidence

ORD record
ord-2e4afacdc5e44c009b05356c39df2ea5
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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