Potassium Carbonate → 3-{3-[2-(4-Methyl-piperidin-1-yl)-ethoxy]-phenyl}-thieno[2,3-d]isoxazole

HRID 8678

반응식

HRID 8678 반응식
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[O:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(#N)C>[CH3:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]([C:11]3[C:15]4[S:16][CH:17]=[CH:18][C:14]=4[O:13][N:12]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:28][CH2:27]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 693814-MethylpiperidineHCID 219835823-[3-(2-Bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole

생성물 1

HCID 219836053-{3-[2-(4-Methyl-piperidin-1-yl)-ethoxy]-phenyl}-thieno[2,3-d]isoxazole수율 96.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
75 °C

실험 절차

Mix 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.250 g, 0.77 mmol), potassium carbonate (0.22 g, 1.59 mmol), 4-methylpiperidine (0.382 g, 3.85 mmol) and acetonitrile (4.0 mL) and heat at 75° C., overnight. Cool the reaction mixture and filter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate). Combine the appropriate fractions and concentrate to give a residue. Purify the residue by column (10 g silica) chromatography using a solvent gradient of dichloromethane to 10% methanol in dichloromethane to obtain the title compound (0.254 g, 96% Yield) as an amber oil. Purity by LC/MS (APCI)=99%, [M+H]+=343.

후처리

  1. temperatureCool the reaction mixture
  2. filtrationfilter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate)
  3. concentrationCombine the appropriate fractions and concentrate
  4. customto give a residue
  5. customPurify the residue by column (10 g silica) chromatography

출처 및 근거

ORD 기록
ord-f27a956677fb4f649e90173553ade153
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091199B1

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