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Potassium Carbonate → N-[3-(5-Chloro-thiophen-2-yl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide

HRID 2079886
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HRID 2079886 반응식
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=2)[C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:34]1[S:35][C:36]([Cl:39])=[CH:37][CH:38]=1.O1CCOCC1>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Cl:39][C:36]1[S:35][C:34]([C:6]2[C:7]3[C:12](=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:9][CH:8]=3)[N:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=2)=[CH:38][CH:37]=1
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참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 761332-Bromo-5-chlorothiopheneHCID 57442204N-(1-Isopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-6-yl)methanesulfonamide

생성물 1

HCID 67100553N-[3-(5-Chloro-thiophen-2-yl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide수율 34.5%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Method J Place N-[1-isopropyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indol-6-yl]-methanesulfonamide (266 mg, 0.70 mmol), potassium carbonate (242 mg, 1.75 mmol), 2-bromo-5-chloro-thiophene (207 mg, 1.05 mmol), dioxane (6 mL) and water (1 mL), followed by addition of tetrakis(triphenylphosphine) palladium (0) (20 mg, 0.018 mmol) in a sealed tube under nitrogen. Heat the reaction mixture at 100° C. overnight, then cool to room temperature. Dilute the reaction mixture with ethyl acetate, and sequentially wash the resulting mixture with water and brine. Dry the organic layer over MgSO4. Chromatograph the crude residue on silica gel column eluting with hexane and ethyl acetate (gradient) to give 89 mg (34%) of the title compound. 1H NMR (CDCl3) δ 7.79 (d, 1H, J=8.8 Hz), 7.42 (d, 1H, J=1.8 Hz), 7.35 (s, 1H), 6.97 (dd, 1H, J=2.0, 8.6 Hz), 6.93 (d, 1H, J=4.0 Hz), 6.88 (d, 1H, J=4.0 Hz), 4.50-4.67 (m, 1H), 2.97 (s, 3H), 1.52 (d, 6H, J=6.6 Hz).

후처리

  1. temperaturecool to room temperature
  2. washsequentially wash the resulting mixture with water and brine
  3. dry with materialDry the organic layer over MgSO4
  4. washChromatograph the crude residue on silica gel column eluting with hexane and ethyl acetate (gradient)

출처 및 근거

ORD 기록
ord-7e52b2b854af4ecbb6a4195e74e07e71
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932284B2

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