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

反応式

HRID 1037267 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 10340Sodium Carbonate溶媒HCID 21863594Toluene ethanol溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8399ac40b0c0400ea3c3bd211e065bbb
出典データセット
uspto-grants-2013_10
特許番号
US08546376B2

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