2-(Tributylstannyl)pyrazine → 4-Methoxy-7-(pyrazin-2-YL)-1H-pyrrolo[2,3-C]pyridine

HRID 606743Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([Sn](CCCC)(CCCC)[C:18]1[CH:23]=[N:22][CH:21]=[CH:20][N:19]=1)CCC>CN(C=O)C.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.[Cu]I>[CH3:12][O:11][C:5]1[CH:4]=[N:3][C:2]([C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 7-bromo-4-methoxy-6-azaindole (1.160 g, 5.11 mmol) and 2-(tri-n-butylstannyl)pyrazine (2.07 g, 5.62 mmol) in 25 mL of dry DMF was degassed with a stream of Ar bubbles for 10 min. To this solution was added tetrakis(triphenylphosphine)palladium (0.590 g, 0.511 mmol) and CuI (0.097 g, 0.511 mmol) and the mixture was heated in a sealed tube at 90° C. for 4 h. The cooled mixture was filtered through methanesulfonic acid SCX cartridges (7×3 g) with MeOH, to remove triphenylphosphine oxide. The filtrate was evaporated and the residue triturated with MeOH to give the title compound (0.612 g, 53%) as a light yellow solid:

Workup

customwas degassed with a stream of Ar bubbles for 10 min
filtrationThe cooled mixture was filtered through methanesulfonic acid SCX cartridges (7×3 g) with MeOH
customto remove triphenylphosphine oxide
customThe filtrate was evaporated
customthe residue triturated with MeOH

Sources & evidence

ORD record: ord-a07fc0e66b1347be8aafff7f8c297070
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915283B2

Reaction notes

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