Hydrochloric Acid → HCID 89812978, 화합물

HRID 1481134노트

반응식

HRID 1481134 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[O:4].C([Sn](CCCC)(CCCC)[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)CCC.O.Cl>CN(C=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.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:9]=2)=[O:4]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 630640Tributyl(2-phenylethynyl)stannaneHCID 89813103Methyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

생성물 1

HCID 89812978HCID 89812978, 화합물수율 104.3%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

A mixture of 7-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (500 mg, 1.77 mmol), tributyl(phenylethynyl)tin (0.8 mL, 2.13 mmol), and PdCl2(PPh3)2 (249 mg, 0.35 mmol) in DMF (18 mL) was heated at 120° C. for 2 h under N2 atmosphere. After cooling the mixture to r.t., water and EtOAc were added. 1 M HCl was added with stirring until pH was ˜2. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined, washed with water, and dried over MgSO4. After evaporating the solvent, the crude product was purified by column chromatography (0-40% EtOAc/hexanes) to give 560 mg of the title compound as a yellow solid. MS: (+) m/z 304.10 (M+1).

후처리

  1. temperatureAfter cooling the mixture to r.t.
  2. extractionThe aqueous layer was extracted with additional EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter evaporating the solvent
  6. customthe crude product was purified by column chromatography (0-40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-56732a7944af4c9e92e2d625ecf15805
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

반응 노트

불러오는 중…