Phenethyl bromide → HCID 178491088, 화합물

HRID 45971

반응식

HRID 45971 반응식
C([N:20]1[C:24]2[CH:25]=[CH:26][C:27]([NH:29][C:30]3C=C[C:33](OC)=[CH:32][CH:31]=3)=[CH:28][C:23]=2[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:48]1([CH2:54][CH2:55]Br)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[CH2:57]1[CH2:61][O:60][CH2:59][CH2:58]1>O>[CH3:59][O:60][C:61]1[CH:57]=[CH:58][C:31]([CH2:30][N:29]([CH2:55][CH2:54][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:27]2[CH:26]=[CH:25][C:24]3[NH:20][CH:21]=[N:22][C:23]=3[CH:28]=2)=[CH:32][CH:33]=1

참가 물질

6

반응물 4

HCID 7666Phenethyl bromideHCID 8028Tetrahydrofuran2회HCID 2733832Lithium HexamethyldisilazideHCID 67445320N1-Trityl-N-(4-methoxyphenyl)benzimidazol-5-amine

생성물 1

HCID 178491088HCID 178491088, 화합물

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

N1-Trityl-N-(4-methoxyphenyl)benzimidazol-5-amine (990 mg; 2 mmol; 1 eq.) was dissolved in THF (5 ml), cooled to 0° C. and treated with lithiumbis(trimethylsilyl)amide 1M in THF (2.4 ml; 2.4 mmol; 1.2 eq.). Phenylethylbromide (0.330 ml; 2.4 mmol; 2.4 eq.) was added and the mixture was stirred at room temperature for 24 h. The mixture was diluted with water and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residue was dissolved in MeOH (5 ml) and treated with TFA (1 ml). After heating to reflux for 1 h the mixture was poured into saturated NaHCO3-solution and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient. Yield: 0.058 g (8.1%); MS m/z: 358.1 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 2.85 (t, 2H, 3J=7.9 Hz); 3.57 (t, 2H, 3J=7.9 Hz); 3.69 (s, 3H); 4.44 (s, 2H); 6.77-6.79 (m, 2H); 6.83-6.86 (m, 2H); 7.14-7.16 (m, 2H); 7.18-7.21 (m, 1H); 7.23-7.25 (m, 2H); 7.28-7.30 (m, 2H); 7.38-7.39 (m, 1H); 7.92 (s, 1H); 11.92 (br s, 1H); HPLC (METHOD [A]): rt 16.74 min (96.3%)

후처리

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated
  4. dissolutionThe residue was dissolved in MeOH (5 ml)
  5. additiontreated with TFA (1 ml)
  6. temperatureAfter heating
  7. temperatureto reflux for 1 h the mixture
  8. additionwas poured into saturated NaHCO3-solution
  9. extractionextracted with ethyl acetate (3×25 ml)
  10. dry with materialThe combined organic layers were dried over Na2SO4
  11. customevaporated
  12. customThe residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient
  13. customrt 16.74 min (96.3%)

출처 및 근거

ORD 기록
ord-3d9fa014f1e84fa8a28a8caf7b5b3ec1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541596B2

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