Sodium Carbonate → 2-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one

HRID 33283

反応式

HRID 33283 の反応式
Br[C:2]1[NH:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:14](=[O:15])[NH:13][CH2:12][CH2:11][C:10]=1[C:9]=23.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.CCO.O>[C:24]1([C:2]2[NH:3][C:4]3[CH:5]=[CH:6][CH:7]=[C:8]4[C:14](=[O:15])[NH:13][CH2:12][CH2:11][C:10]=2[C:9]=34)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 99432302-Bromo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one

生成物 1

HCID 102208822-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

実験手順

Tricyclic bromide 11 (0.2 g, 0.75 mmol) in toluene (20 mL) and EtOH (10 mL) was treated with solid Na2CO3 (0.199 g, 1.88 mmol), LiCl (0.095 g, 2.25 mmol), phenylboronic acid (0.138 g, 1.13 mmol), and water (0.50 mL). The solution was degassed and tetrakis(triphenylphosphine)palladium(0) (43 mg, 5 mol %) was added. The solution was heated at reflux for 5 h, and then cooled to ambient temperature and diluted with water (20 mL). The aqueous layer was adjusted to pH=7-8 with saturated aqueous K2CO3 and extracted with EtOAc (20 mL×3). The organic solution was washed with water and brine, and dried (Na2SO4), filtered, and concentrated. The crude product was recrystallized (CH2Cl2/MeOH/hexanes) to yield the 2-phenyltricycle as a pale-yellow solid, 183 mg (93%). mp 249-255° C. (dec); 1H NMR (CDCl3/CD4OD) δ 3.14 (m, 2H), 3.53 (m, 2H), 7.23 (t, 1H, J=7.7 Hz), 7.33 (m, 1H), 7.44 (m, 2H), 7.55 (m, 3H), 7.83 (d, 1H, J=7.7 Hz); HRMS (M+H) Calcd for C17H14N2O+H, 263.1184, Found: 263.1189; Anal. (C17H14N2O.0.8 H2O) C, H, N.

後処理

  1. customThe solution was degassed
  2. additiontetrakis(triphenylphosphine)palladium(0) (43 mg, 5 mol %) was added
  3. temperatureThe solution was heated
  4. temperatureat reflux for 5 h
  5. additiondiluted with water (20 mL)
  6. extractionextracted with EtOAc (20 mL×3)
  7. washThe organic solution was washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was recrystallized (CH2Cl2/MeOH/hexanes)
  12. customto yield the 2-phenyltricycle as a pale-yellow solid, 183 mg (93%)

出典と根拠

ORDレコード
ord-57b7dd231f264c7992b6af664dc905d3
出典データセット
uspto-grants-2008_09
特許番号
US07429578B2

関連ノート

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