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

HRID 2079886
ノート
印刷プレビュー

反応式

HRID 2079886 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7e52b2b854af4ecbb6a4195e74e07e71
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932284B2

反応ノート

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