3-bromo-2-phenyl-4H-chromen-4-one → {1-[4-(4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037267

반응식

HRID 1037267 반응식
Br[C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]([O:23][C:24](=[O:45])[NH:25][C:26]1([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][CH:31]=2)[CH2:29][CH2:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[C:19]([O:23][C:24](=[O:45])[NH:25][C:26]1([C:30]2[CH:31]=[CH:32][C:33]([C:2]3[C:7](=[O:8])[C:6]4[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=4[O:4][C:3]=3[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:34][CH:35]=2)[CH2:27][CH2:28][CH2:29]1)([CH3:22])([CH3:20])[CH3:21]

참가 물질

5

반응물 2

HCID 4662783-bromo-2-phenyl-4H-chromen-4-oneHCID 58326444tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate

생성물 1

HCID 67067804{1-[4-(4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester수율 94%

시약·촉매·용매 2

HCID 10340Sodium Carbonate용매HCID 21863594Toluene ethanol용매

반응 조건

온도
80 °C

실험 절차

To a round-bottom flask was added 3-bromo-2-phenyl-1-benzopyran-4-one (27.1 mg, 0.09 mmol) and {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (50.4 mg, 0.135 mmol) in toluene:ethanol (4:1, 2.5 mL) and 2 M aqueous sodium carbonate (1 mL). The solution was degassed for 20 minutes, after which time, tetrakis(triphenylphosphine) palladium (5.2 mg, 5 mol %) was added. The reaction mixture was heated to 80° C. using an oil bath with a water cooled reflux condenser, while stirring for 21 hours. The reaction mixture cooled to RT, suspended in ethyl acetate and washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (10:1 to 5:1 hexane:EtOAc gradient) to give a white solid (12.2 mg, 94%). 1H-NMR (400 MHz, CDCl3) δ 8.30 (d, 1H), 7.66 (dd, 1H), 7.53 (dd, 1H), 7.38-7.45 (m, 3H), 7.30-7.36 (m, 3H), 7.27 (d, 2H), 7.19 (d, 2H), 5.11 (bs, 1H), 2.35-2.58 (m, 4H), 1.91-2.09 (m, 1H), 1.77-1.88 (m, 1H), 1.38 (bs, 9H).

후처리

  1. customThe solution was degassed for 20 minutes
  2. additionafter which time, tetrakis(triphenylphosphine) palladium (5.2 mg, 5 mol %) was added
  3. temperaturecooled
  4. temperaturereflux condenser
  5. temperatureThe reaction mixture cooled to RT
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified by silica gel chromatography (10:1 to 5:1 hexane:EtOAc gradient)

출처 및 근거

ORD 기록
ord-8399ac40b0c0400ea3c3bd211e065bbb
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546376B2

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