Sodium Carbonate → (R)-4-dimethylamino-1-[2-methyl-3-(2-(triethylsilyl)-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

HRID 2064536노트

반응식

HRID 2064536 반응식
[CH3:1][N:2]([CH3:29])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][C:6]([CH2:10][C@H:11]([CH3:22])[CH2:12][C:13]#[C:14][Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])([OH:9])[CH2:5][CH2:4]1.I[C:31]1[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=1[NH2:33].C(=O)([O-])[O-].[Na+].[Na+]>O=O.O.C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-2](Cl)C1C(Cl)=CC=CN=1)(C)C>[CH3:29][N:2]([CH3:1])[C:3]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:8][CH2:7][C:6]([CH2:10][C@H:11]([CH3:22])[CH2:12][C:13]2[C:34]3[C:32](=[CH:31][CH:37]=[CH:36][CH:35]=3)[NH:33][C:14]=2[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])([OH:9])[CH2:5][CH2:4]1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 119952-IodoanilineHCID 131729994(R)-4-dimethylamino-1-(2-methyl-5-(triethylsilyl)pent-4-inyl)-4-phenylcyclohexanol

생성물 1

HCID 68629968(R)-4-dimethylamino-1-[2-methyl-3-(2-(triethylsilyl)-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

시약·촉매·용매 3

HCID 178439027HCID 178439027, 화합물촉매HCID 962Water용매HCID 977Oxygen용매

실험 절차

A solution of (R)-4-dimethylamino-1-(2-methyl-5-(triethylsilyl)pent-4-inyl)-4-phenylcyclohexanol (106 mg, 0.25 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 34 mg, 0.05 mmol), 2-iodoaniline (68 mg, 0.31 mmol) and sodium carbonate (136 mg, 1.28 mmol) in oxygen- and water-free N,N-dimethylformamide (5 mL) was stirred for 18 h at 100° C. The reaction mixture was concentrated to low volume in a vacuum, the residue mixed with toluol several times and the mixture concentrated to low volume again in each case. This residue was distributed between water and ethyl acetate (10 mL each), the phases were separated and the aqueous phase extracted with ethyl acetate (3×10 mL). The combined organic phases were washed with 1 M sodium thiosulphate solution and water (10 mL each), dried with sodium sulphate, filtered and concentrated to low volume in a vacuum. The raw product was purified by flash chromatography (10 g, 20×1.5 cm) with ethyl acetate/cyclohexane (1:2).

후처리

  1. concentrationThe reaction mixture was concentrated to low volume in a vacuum
  2. additionthe residue mixed with toluol several times
  3. concentrationthe mixture concentrated to low volume again in each case
  4. customthe phases were separated
  5. extractionthe aqueous phase extracted with ethyl acetate (3×10 mL)
  6. washThe combined organic phases were washed with 1 M sodium thiosulphate solution and water (10 mL each)
  7. dry with materialdried with sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to low volume in a vacuum
  10. customThe raw product was purified by flash chromatography (10 g, 20×1.5 cm) with ethyl acetate/cyclohexane (1:2)

출처 및 근거

ORD 기록
ord-79b865d741b44ff5b2c1040a14b673a7
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288430B2

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