Sodium Carbonate → HCID 17965980, 화합물

HRID 1348887

반응식

HRID 1348887 반응식
Cl[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl.C(O)C>[Cl:15][C:16]1[CH:21]=[C:20]([C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=2)[CH:19]=[CH:18][CH:17]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 83343Methyl 2-chloro-4-nitrobenzoateHCID 2734323(3-Chlorophenyl)boronic acid

생성물 1

HCID 17965980HCID 17965980, 화합물수율 99.4%

시약·촉매·용매 4

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of methyl 2-chloro-4-nitrobenzoate (0.432 g, 2.0 mmol), 3-chlorophenylboronic acid (0.375 g, 2.4 mmol), trans-dichlorobis(tricyclohexylphosphine)-palladium (II) (0.074 g, 0.1 mmol), and sodium carbonate (0.64 g, 6.0 mmol) in a mixture of toluene (10 mL), dioxane (10 mL), and ethanol (2 mL) was heated to reflux for 12 hours, cooled to room temperature, diluted with ethyl acetate (10 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:10 ethyl acetate/hexanes to provide 0.58 g (99%) of the desired product. MS (DCI/NH3) m/z 309 (M+NH4)+; 1H NMR (CDCl3) δ 8.27-8.22 (m, 2H), 8.00 (dd, 1H), 7.41-7.34 (m, 3H), 7.23-7.18 (m, 1H), 3.72 (s, 3H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 1:10 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-eba5564ff91749a7a04dedf78fcc2c06
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211595B2

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