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Potassium Carbonate → Methyl 6-chloro-5-(4-(1-(hydroxymethyl)cyclobutyl)-3-methoxyphenyl)-1h-indole-3-carboxylate

HRID 1054853
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HRID 1054853 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9]2)=[C:4]([O:14][CH3:15])[CH:3]=1.[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][NH:23]2)=[CH:19][C:18]=1B1OCC(C)(C)CO1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][NH:23]2)=[CH:19][C:18]=1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9]2)=[C:4]([O:14][CH3:15])[CH:3]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylateHCID 86698841[1-(4-Bromo-2-methoxyphenyl)cyclobutyl]methanol

생성물 1

HCID 86698842Methyl 6-chloro-5-(4-(1-(hydroxymethyl)cyclobutyl)-3-methoxyphenyl)-1h-indole-3-carboxylate수율 83.4%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a mixture of [1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol (180 mg, 0.660 mmol) in dioxane (10 mL) and water (4 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (213 mg, 0.660 mmol), Pd (dppf)Cl2 (48 mg, 0.070 mmol) and potassium carbonate (273 mg, 2.00 mmol). The reaction mixture was purged with nitrogen for 3 minutes and stirred at 80° C. for 2 hours. The mixture was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (220 mg, 83%) as a brown solid. It was used for next step without further purification.

후처리

  1. customThe reaction mixture was purged with nitrogen for 3 minutes
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-460559aebe2b4c2ea21c3aa5e5fc2279
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394285B2

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