Potassium Carbonate → 9-[(2,6-Dichlorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3h)-one

HRID 51424

반응식

HRID 51424 반응식
[C:1]([C:5]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:6]=1[C:7]1[C:8](=[O:18])[CH2:9][CH2:10][CH2:11][C:12]=1[NH:13]2)([O:3][CH3:4])=[O:2].[CH:19]1[CH:24]=[C:23]([Cl:25])[C:22]([CH2:26]Br)=[C:21]([Cl:28])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:25][C:23]1[CH:24]=[CH:19][CH:20]=[C:21]([Cl:28])[C:22]=1[CH2:26][N:13]1[C:12]2[CH2:11][CH2:10][CH2:9][C:8](=[O:18])[C:7]=2[C:6]2[C:14]1=[CH:15][CH:16]=[CH:17][C:5]=2[C:1]([O:3][CH3:4])=[O:2]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 11368514methyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-5-carboxylate

생성물 1

HCID 227394759-[(2,6-Dichlorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3h)-one수율 56%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 5-carbomethoxy-1,2-dihydro-9H-carbazol-4(3H)-one (973 mg, 4.0 mM), a-bromo-2,6-dichlorotoluene (1.19 g, 4.8 mM), and potassium carbonate (553 mg, 4.0 mM) in 10 mL DMF was stirred at room temperature for 24 hours. The mixture was diluted with ethyl acetate, washed with H2O, 1 N HCl, H2O, saturated NaHCO3, H2O, and saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated. The residue was purified by column chromatography on silica gel (elution with methylene chloride/ethyl acetate) to afford 900 mg (56%) of the 9-[(2,6-dichlorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one as a white foam. 1H NMR (CDCl3) δ7.4-7.2 (m, 6H), 5.6 (s, 2H), 4.0 (s, 3H), 2.9 (t, 2H, J=6 Hz), 2.55 (t, 2H, J=6 Hz), and 2.2 (m, 2H). IR (KBr, cm−1) 1725 and 1652. MS (ES) m/e 400, 402, 404.

후처리

  1. washwashed with H2O, 1 N HCl, H2O, saturated NaHCO3, H2O, and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (elution with methylene chloride/ethyl acetate)

출처 및 근거

ORD 기록
ord-f8de611e94054df88fcb4dfdaca88848
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713645B1

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