Cesium carbonate → 4-(5,8,8-Trimethyl-7,8-dihydro-naphthalen-2-yl-amino)-benzoic acid ethyl ester

HRID 1795599

반응식

HRID 1795599 반응식
[CH3:1][C:2]1[C:3]2[CH:4]=[CH:5][C:6]([NH2:14])=[CH:7][C:8]=2[C:9]([CH3:13])([CH3:12])[CH2:10][CH:11]=1.Br[C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=C(C3C4C(=CC=CC=4)C=CC=3)C3C(C=2)=CC=CC=3)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:23]([O:22][C:20](=[O:21])[C:19]1[CH:25]=[CH:26][C:16]([NH:14][C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:1])=[CH:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[CH:17][CH:18]=1)[CH3:24]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 22043Ethyl 4-bromobenzoateHCID 18630801Bis(diphenylphosphino)-1,1'-binaphthylHCID 22218345HCID 22218345, 화합물2회

생성물 1

HCID 210243674-(5,8,8-Trimethyl-7,8-dihydro-naphthalen-2-yl-amino)-benzoic acid ethyl ester

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

General Procedure L To a solution of 5,8,8-trimethyl-7,8-dihydro-naphthalen-2-yl-amine (Compound 64, 0.33 g, 1.8 mmol) and ethyl 4-bromobenzoate (0.52 g, 2.3 mmol) in 10.0 mL of toluene while stirring under argon were added cesium carbonate (0.89 g, 2.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 33 mg, 0.04 mmol) and bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 47 mg, 0.08 mmol) consecutively. The reaction was then heated at 100° C. for 24 h. The reaction was then cooled to room temperature, diluted with water and extracted 2 times with ethyl ether. The combined organic extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed in vacuo. The crude product was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give the title compound as a yellow solid.

후처리

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted 2 times with ethyl ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed in vacuo
  7. customThe crude product was purified by silica gel chromatography (10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-079a93512d444eb4a575adc250df4e07
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026487B2

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