Triethylamine → 7-phenylethynyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1677398

Reaction equation

HRID 1677398 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[NH:4][CH:3]=1.[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)#[CH:24].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[C:25]1([C:23]#[C:24][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=4)[N:9]=3)[NH:4][CH:3]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 595405187-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 595405547-phenylethynyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazineYield 90.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

7-Iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (500 mg, 1.22 mmol), PdCl2(PPh3)2 (43 mg, 0.061 mmol), and cuprous iodide (6 mg, 0.031 mmol) were added to a 20 ml microwave vial. The vial was capped and purged with nitrogen. Ethynyl benzene (0.4 ml, 3.6 mmol), triethylamine (5 ml) and N,N-dimethylformamide (5 ml) were added through the septum and the vial was purged again with nitrogen. The mixture was heated in a microwave reactor at 70° C. for 30 minutes. The crude mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid and water/brine. The organic layer was filtered through celite and concentrated. The residue was triturated with a mixture of ethyl acetate and hexanes and filtered, washed with hexanes, and dried to give 427 mg of 7-phenylethynyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine. MS: (M+H)+=386.

Workup

  1. customThe vial was capped
  2. custompurged with nitrogen
  3. customthe vial was purged again with nitrogen
  4. additionThe crude mixture was diluted with ethyl acetate
  5. washwashed with dilute hydrochloric acid and water/brine
  6. filtrationThe organic layer was filtered through celite
  7. concentrationconcentrated
  8. customThe residue was triturated with a mixture of ethyl acetate and hexanes
  9. filtrationfiltered
  10. washwashed with hexanes
  11. customdried

Sources & evidence

ORD record
ord-81041fa797e4461fbdc67bde952b713e
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Linked notes

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