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

HRID 1677401

Reaction equation

HRID 1677401 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)[N:4]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:3]=1.C(N(CC)CC)C.CN(C=O)C.[C:45]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)#[CH:46]>C(OCC)(=O)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>[C:47]1([C:45]#[C:46][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)[N:4]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:3]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 595407447-iodo-5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 595406337-phenylethynyl-5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazineYield 73.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

7-Iodo-5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (275 mg, 0.49 mmol), PdCl2(PPh3)2 (17 mg, 0.02 mmol), and cuprous iodide (5 mg, 0.02 mmol) were placed in a 5 ml microwave vial. The vial was capped and purged with nitrogen. Triethylamine (0.35 ml, 2.45 mmol) and 2.5 ml of DMF were added through the septum and the flask was purged again with nitrogen three times. Ethynyl-benzene (0.19 ml, 1.75 mmol) was added and the reaction was heated in a microwave reactor at 100° C. for 30 minutes. The crude reaction mixture was diluted with ethyl acetate, washed with water two times, dried and concentrated. The mixture was purified by flash chromatography using a gradient of 0% ethyl acetate in hexanes up to 30% to yield 195 mg of 7-phenylethynyl-5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine. MS: (M+H)+=540.

Workup

  1. customThe vial was capped
  2. custompurged with nitrogen
  3. customthe flask was purged again with nitrogen three times
  4. customThe crude reaction mixture
  5. washwashed with water two times
  6. customdried
  7. concentrationconcentrated
  8. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-a6c468f6af774643b25cb817a1dae963
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Linked notes

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