Cesium carbonate → 3-Cyclopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 1015638

반응식

HRID 1015638 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1Br)=[O:4].[CH:17]1([NH2:20])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:20][CH:17]1[CH2:19][CH2:18]1)=[O:4]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 69828CyclopropylamineHCID 634876Binap, (A+-)-HCID 20775762Methyl 3-bromo-5-phenyl-thiophene-2-carboxylate

생성물 1

HCID 207757643-Cyclopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester수율 22%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

To a solution of 3-Bromo-5-phenyl-thiophene-2-carboxylic acid methyl ester (250 mg, 0.89 mmol) in toluene (25 ml) was added cyclopropylamine (57 mg, 1.0 mmol), cesium carbonate (382 mg, 1.2 mmol), BINAP (50 mg, 0.08 mmol) and tris (dibenzyli-denacetone)dipaladium (0) (38 mg, 0.04 mmol). The reaction mixture was stirred for 16 h at 110° C. in a sealed tube. The mixture was partitioned between toluene (20 mL) and water (20 mL) and the organic layer was separated. The aqueous phase was washed twice with toluene (2×10 mL) and the combined toluene layer was dried (MgSO4), concentrated and the residue was purified by preparative chromatography (10% EtOAc/Hexane) to obtain 52 mg (22%) of 3-Cyclopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): 7.67-7.62 ppm (m, 2H, Haro); 7.43-7.32 ppm (m, 3H, Haro); 7.16 ppm (s, 1H, Haro); 3.82 ppm (S, 3H); 2.65 ppm (m, 1H); 0.62 ppm (m, 2H); 0.35 ppm (m, 2H).

후처리

  1. customThe mixture was partitioned between toluene (20 mL) and water (20 mL)
  2. customthe organic layer was separated
  3. washThe aqueous phase was washed twice with toluene (2×10 mL)
  4. dry with materialthe combined toluene layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified by preparative chromatography (10% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-78c2b097b9ca481783350ce25cc76f74
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985769B2

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