Sodium Carbonate → HCID 70269200, 화합물

HRID 1598343

반응식

HRID 1598343 반응식
[OH:1]C1C=CC2C3C(=CC(O)=CC=3)C(=O)C=2C=1.Br[C:18]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:19]=1[C:20](OC)=O.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(COC)OC>[CH3:29][O:28][C:25]1[C:24](=[O:1])[C:19]2[C:18](=[CH:27][CH:26]=1)[C:35]1[C:34](=[CH:33][C:32]([O:31][CH3:30])=[CH:37][CH:36]=1)[CH:20]=2

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 2776849Methyl 2-bromo-5-methoxybenzoateHCID 43541812,7-Dihydroxyfluoren-9-one

생성물 1

HCID 70269200HCID 70269200, 화합물

시약·촉매·용매 2

HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

Prepared analogously to 2-[9-(2-Methoxyfluorenyl)]ethylamine hydrochloride in Example 1 beginning with 2,7-dihydroxy-9-fluorenone. 1H NMR (300 MHz, CDCl3) δ 7.60 (d, J=8.0 Hz, 2H), 7.00 (d, J=2.0 Hz, 2H), 7.85 (dd, J=8.0, 2.0 Hz, 2H), 3.90-4.10 (m, 1H), 3.85 (s, 6H), 2.50-2.60 (m, 2H), 2.10-2.30 (m, 2H). Alternatively, the necessary intermediate 2,7-dimethoxyfluorenone was prepared as follows: Methyl 2-bromo-5-methoxybenzoate (1.60 g, 6.53 mmol), 4-methoxyphenylboronic acid (1.30 g, 8.55 mmol), and tris(dibenzylideneacetone) dipalladiurn (0) (0.20 g, 0.22 mmol) were added to dimethoxyethane (25 mL) and 2M sodium carbonate (25 mL). The reaction was stirred at reflux for 16 h then decanted and the residue extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and the solvent removed by rotary evaporation to afford 1.50 g of the coupled product (5.51 mmol, 84% yield). The ester (10.80 g, 39.70 mmol) was hydrolyzed with 1N sodium hydroxide (80 mL) in refluxing ethanol (500 mL). The cooled reaction mixture was extracted with methylene chloride and then acidified with 1N hydrochloric acid. The acidic solution was then extracted with methylene chloride. The organic layers were combined and the solvent was dried and concentrated by rotary evaporation to give 9.00 g (34.88 mmol, 88% yield) of the acid. 9.00 g (34.88 mmol) of the acid was dissolved in thionyl chloride (250 mL) and stirred at reflux for 6 h. The reaction was cooled to ambient temperature and the solvent was removed by rotary evaporation to give 8.20 g of 2,7-dimethoxyfluorenone (34.17 mmol, 98% yield) as a red solid.

후처리

  1. temperatureat reflux for 16 h
  2. customthen decanted
  3. extractionthe residue extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customthe solvent removed by rotary evaporation

출처 및 근거

ORD 기록
ord-6905c89d33f9490c8a20786dc98a4d35
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05736578

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