Triethylamine → 6-(3-methoxy-4-methoxymethoxy-phenyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole

HRID 1861048

반응식

HRID 1861048 반응식
I[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])(=[O:13])=[O:12])=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[O:31][CH2:32][O:33][CH3:34].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][N:8]3[S:11]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])(=[O:13])=[O:12])=[CH:4][CH:3]=2)[CH:28]=[CH:29][C:30]=1[O:31][CH2:32][O:33][CH3:34]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 218773966-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazoleHCID 21877521HCID 21877521, 화합물

생성물 1

HCID 218773546-(3-methoxy-4-methoxymethoxy-phenyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

A mixture of 6-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole (5.78 g, 13.56 mmol, 1.00 equiv) and 3-methoxy-4-(methoxymethoxy)benzene-boronic acid (3.45 g, 16.27 mmol, 1.20 equiv) under argon was dissolved in dioxane (15 mL) and water (2.0 mL). To this solution was added triethylamine (2.83 mL, 20.3 mmol, 1.5 equiv), potassium carbonate (2.8 g, 20.3 mmol, 1.5 equiv) and dichlorobis(triphenylphosphine)palladium (476 mg, 0.678 mmol, 0.05 equiv). The reaction mixture was heated to 90° C. for 2 h and then was cooled to 23° C. The mixture was separated between ethyl acetate (250 mL) and saturated sodium bicarbonate (150 mL). The organic material was dried over sodium sulfate, decanted and concentrated under reduced pressure to give crude 6-(3-methoxy-4-methoxymethoxy-phenyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole that was dried under high vacuum for 15 h and was used without further purification.

후처리

  1. temperaturewas cooled to 23° C
  2. customThe mixture was separated between ethyl acetate (250 mL) and saturated sodium bicarbonate (150 mL)
  3. dry with materialThe organic material was dried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2cfaeafbc4ce4e6dbe5a928592b2a42b
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531491B1

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