Trimethylsilylacetylene → Cyclopropyl-(5''-trimethylsilanylethynyl-[2,2';4',3'']terpyridin-6'-yl)-amine

HRID 1798512Notes

Reaction equation

HRID 1798512 reaction equation
CNC1N=C(C2C=CC=CN=2)C=C(C2C=NC=C(C#CC3N(C)C=NC=3)C=2)C=1.Br[C:30]1[CH:31]=[C:32]([C:36]2[CH:41]=[C:40]([NH:42][CH:43]3[CH2:45][CH2:44]3)[N:39]=[C:38]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=3)[CH:37]=2)[CH:33]=[N:34][CH:35]=1.[C:52]([Si:54]([CH3:57])([CH3:56])[CH3:55])#[CH:53]>>[CH:43]1([NH:42][C:40]2[N:39]=[C:38]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=3)[CH:37]=[C:36]([C:32]3[CH:33]=[N:34][CH:35]=[C:30]([C:53]#[C:52][Si:54]([CH3:57])([CH3:56])[CH3:55])[CH:31]=3)[CH:41]=2)[CH2:45][CH2:44]1

Participants

4

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 44135953(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-cyclopropyl-amineHCID 86633650Methyl-[5''-(3-methyl-3H-imidazol-4-ylethynyl)-[2,2';4',3'']terpyridin-6'-yl]-amine

Product 1

HCID 68947114Cyclopropyl-(5''-trimethylsilanylethynyl-[2,2';4',3'']terpyridin-6'-yl)-amine

Procedure

is prepared analogously to Methyl-[5″-(3-methyl-3H-imidazol-4-ylethynyl)-[2,2′;4′,3″]terpyridin-6′-yl]-amine (Example 2.182) by replacing (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-methyl-amine (Example 2.1; step 1) with (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-cyclopropyl-amine (Example 1.26) and by replacing 1-methyl-5-((trimethylsilyl)ethynyl)-1H-imidazole with ethynyl-trimethyl-silane to afford the title compound; [M+H]+ 385.

Sources & evidence

ORD record
ord-f7503e2d0ad344feb35e2912bd5df538
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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