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

HRID 1677401

반응식

HRID 1677401 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a6c468f6af774643b25cb817a1dae963
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008298B2

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