2-(Tributylstannyl)pyrazine → 2-(Methylsulfanyl)-7-(pyrazin-2-yl)pyrrolo[2,1-f][1,2,4]triazine

HRID 1262445Notes

Reaction equation

HRID 1262445 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)CCC.Br[C:21]1[N:29]2[C:24]([CH:25]=[N:26][C:27]([S:30][CH3:31])=[N:28]2)=[CH:23][CH:22]=1>>[CH3:31][S:30][C:27]1[N:26]=[CH:25][C:24]2=[CH:23][CH:22]=[C:21]([C:6]3[CH:11]=[N:10][CH:9]=[CH:8][N:7]=3)[N:29]2[N:28]=1

Participants

3

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 574161287-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 574161252-(Methylsulfanyl)-7-(pyrazin-2-yl)pyrrolo[2,1-f][1,2,4]triazineYield 44.9%

Procedure

Analogous to Example 1562a, 2-Tributylstannanyl-pyrazine (0.650 mL, 2.06 mmol) and 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.224 g, 0.916 mmol) were reacted to afford 2-Methylsulfanyl-7-pyrazin-2-yl-pyrrolo[2,1-f][1,2,4]triazine (0.100 g, 44%). 1H-NMR (DMSO-d6): 9.87 (s, 1H), 9.50 (s, 2H), 9.15 (s, 1H), 8.80 (m, 6H), 8.62 (s, 1H), 7.64 (d, 1H, J=4.96 Hz), 7.17 (d, 1H, J=4.96 Hz), 2.66 (s, 4H).

Sources & evidence

ORD record
ord-f58eef30ed044ae4889ccb3a7c9da3a0
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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