Tetrahydrofuran → 2-((4-(3-(4-Bromophenyl)benzo[d]isothiazol-6-yl)-2-methylbut-3-yn-2-yl)(ethyl)amino)ethanol

HRID 270458노트

반응식

HRID 270458 반응식
C(OP(=O)(OCC)O[C:6]([CH3:26])([CH3:25])[C:7]#[C:8][C:9]1[CH:24]=[CH:23][C:12]2[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)=[N:14][S:15][C:11]=2[CH:10]=1)C.[CH2:31]([NH:33][CH2:34][CH2:35][OH:36])[CH3:32].C1COCC1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[Br:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[C:12]3[CH:23]=[CH:24][C:9]([C:8]#[C:7][C:6]([N:33]([CH2:31][CH3:32])[CH2:34][CH2:35][OH:36])([CH3:25])[CH3:26])=[CH:10][C:11]=3[S:15][N:14]=2)=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 80722-(Ethylamino)ethanolHCID 516892Sodium BicarbonateHCID 69289237Phosphoric acid 3-[3-(4-bromo-phenyl)-benzo [d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl ester diethyl ester

생성물 1

HCID 102972032-((4-(3-(4-Bromophenyl)benzo[d]isothiazol-6-yl)-2-methylbut-3-yn-2-yl)(ethyl)amino)ethanol

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

To 45 mg (0.09 mmol) Phosphoric acid 3-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl ester diethyl ester and 16 μl (0.18 mmol) 2-Ethylaminoethanol in 0.5 ml THF 10.2 mg (0.01 mmol) tetrakis(triphenylphosphine)palladium was added and the suspension stirred at 50° C. over night. The mixture was added to a saturated aqueous solution of NaHCO3 and EtOAc, the phases were separated and the inorganic one was extracted with EtOAc. The combined organic phases were washed with brine and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2:MeOH 95:5 gave 2-((3-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl)-ethyl-amino)-ethanol as yellow semisolid, MS: 443 (MH+, 1Br).

후처리

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-57cd6617c62348b598c141f5b80936e9
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449483B2

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