2-(Tributylstannyl)pyrazine → HCID 57590475, compound

HRID 1783387Notes

Reaction equation

HRID 1783387 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11](=[O:32])[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:21](=[O:31])[C:22](=[O:30])[C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16][CH2:15]1)=[O:13].C([Sn](CCCC)(CCCC)[C:40]1[CH:45]=[N:44][CH:43]=[CH:42][N:41]=1)CCC>O1CCOCC1.CCOC(C)=O.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>[N:41]1[CH:42]=[CH:43][N:44]=[CH:45][C:40]=1[C:2]1[N:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11](=[O:32])[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:21](=[O:31])[C:22](=[O:30])[C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16][CH2:15]1)=[O:13]

Participants

6

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 57590468HCID 57590468, compound

Product 1

HCID 57590475HCID 57590475, compoundYield 7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 3-[4-[2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetyl]piperazin-1-yl]-4-phenyl-cyclobut-3-ene-1,2-dione (0.030 g, 0.057 mmol) and 2-tributylstannylpyrazine (0.025 g, 0.069 mmol) in dioxane (3 mL) was purged with Ar and then Pd(PPh3)4 (0.020 g, 0.017 mmol) was added, the reactor was sealed and the mixture was heated at 90° C. for 16 h. The cooled reaction mixture was diluted with EtOAc, washed (1M aqueous KF, brine), dried (Na2SO4) and evaporated to give a solid. Purification of this material by preparative HPLC (C-18/10-90% MeCN-5 mmolar aqueous NH4OAc) gave the title compound (0.002 g, 7%) as a yellow solid:

Workup

  1. customthe reactor was sealed
  2. customThe cooled reaction mixture
  3. washwashed (1M aqueous KF, brine)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a solid
  7. customPurification of this material by preparative HPLC (C-18/10-90% MeCN-5 mmolar aqueous NH4OAc)

Sources & evidence

ORD record
ord-0a802b3ca9524f2a8f42c6e306d1dcbd
Source dataset
uspto-grants-2009_03
Patent number
US07501419B2

Reaction notes

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