3-Nitrophenylboronic Acid → 5-(3-nitrophenyl)-1,3-dihydro-2H-indol-2-one

HRID 6980

반응식

HRID 6980 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:12]([C:15]1[CH:20]=[C:19]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[CH2:5]3)[CH:18]=[CH:17][CH:16]=1)([O-:14])=[O:13]

참가 물질

7

반응물 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 6111935-Bromo-2-oxindole

생성물 1

HCID 102206615-(3-nitrophenyl)-1,3-dihydro-2H-indol-2-one수율 65%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

5-bromo-2-indolinone (1.08 g, 5.09 mmol) and tetrakistriphenyl phosphine Pd (0) (0.273 g) were stirred under an atmosphere of nitrogen in ethylene glycol dimethyl ether (35 mL). After 15 minutes, 3-nitrophenyl boronic acid (1.70 g, 10.2 mmol) was added, followed by potassium carbonate (4.24 g, 30.7 mmol) in water (15 mL). The reaction was heated to reflux overnight, cooled to room temperature and then filtered. Saturated ammonium chloride was added. The water layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried with MgSO4, filtered, and solvent removed in vacuo. The product was purified by flash silica gel chromatography (3:2 hexane; ethyl acetate) to give 5-(3-Nitro-phenyl)-1,3-dihydro-indol-2-one (0.084 g, 65%), Mp=269° C.; 1H NMR (DMSO) δ 10.5 (s, 1H), 8.38–8.36 (m, 1H) 8.17–8.14 (m, 1H), 8.10–8.07 (m, 1H), 7.75–7.60 (m, 3H), 6.95 (d, 1H, J=8.1 Hz), 3.57 (s, 2H); IR (KBr) 3420, 3190, 1700 cm−1; MS (EI) m/z 253 (M−H)−; CHN calculated for C14H10N2O: C, 66.14; H, 3.96; N, 11.02; Found: C, 64.59; H, 4.16; N, 9.43.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. additionSaturated ammonium chloride was added
  5. extractionThe water layer was extracted with ethyl acetate (3×20 mL)
  6. dry with materialThe combined organic layer was dried with MgSO4
  7. filtrationfiltered
  8. customsolvent removed in vacuo
  9. customThe product was purified by flash silica gel chromatography (3:2 hexane; ethyl acetate)

출처 및 근거

ORD 기록
ord-73b578707101440ab23e494441247e5a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084168B2

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