Tricyclohexylphosphine → tert-Butyl (4-cyclopropyl-2-methylphenyl)carbamate

HRID 2400275노트

반응식

HRID 2400275 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=1.O.[CH:18]1(B(O)O)[CH2:20][CH2:19]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:18]1([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=2)[CH2:20][CH2:19]1

참가 물질

9

반응물 4

HCID 75806TricyclohexylphosphineHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 23074904N-Boc-4-iodo-2-methylanilineHCID 66762321Cyclopropylboronic acid monohydrate

생성물 1

HCID 86665748tert-Butyl (4-cyclopropyl-2-methylphenyl)carbamate수율 86.5%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A mixture of tert-butyl (4-iodo-2-methylphenyl)carbamate (1.04 g), cyclopropylboronic acid monohydrate (422 mg), palladium(II) acetate (35.1 mg), tricyclohexylphosphine (87.5 mg), tripotassium phosphate monohydrate (2.52 g), toluene (8.7 mL), and water (0.87 mL) was stirred at 100° C. for 15 hours. The reaction mixture was left to cool and then diluted with ethyl acetate and filtered through Celite (registered trademark). The filtrate was washed with brine and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (668 mg). 1H-NMR (CDCl3) δ ppm: 0.55-0.70 (2H, m), 0.80-1.00 (2H, m), 1.51 (9H, s), 1.75-1.90 (1H, m), 2.21 (3H, s), 5.85-6.45 (1H, br), 6.75-7.00 (2H, m), 7.45-7.75 (1H, m).

후처리

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. filtrationfiltered through Celite (registered trademark)
  4. washThe filtrate was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-1badeb70f9d44589a8fd3ae977055fad
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796247B2

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