2-(Hydroxymethyl)-1H-benzimidazole → HCID 69295003, 화합물

HRID 899684

반응식

HRID 899684 반응식
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:15][OH:16].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:5]1([CH2:4][N:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=[C:7]2[CH2:15][OH:16])[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 785692-(Hydroxymethyl)-1H-benzimidazoleHCID 81503BromomethylcyclopropaneHCID 81531Diisopropylethylamine

생성물 1

HCID 69295003HCID 69295003, 화합물수율 26%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of (bromomethyl)cyclopropane (0.39 mL, 4.02 mmol) and (1H-benzoimidazol-2-yl)-methanol (596 mg, 4.02 mmol) in DMF (10 mL) was added N,N-diisopropylethylamine (0.84 mL, 4.82 mmol). The reaction mixture was stirred at 60° C. for 3 days. Then it was cooled to room temperature and quenched with saturated NaHCO3 (15 mL) and the phases were separated. The aqueous phase was washed with CH2Cl2 (3×20 mL). Then the combined organic layers were washed with brine (2×30 mL), dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a dark brown oil. Purification by flash column chromatography on silica gel using 2% CH3OH/CH2Cl2 afforded the product as a yellow solid (210 mg, 26%). 1H NMR (CDCl3) δ 0.40-0.45 (m, 2H), 0.52-0.61 (m, 2H), 1.22-1.33 (m, 1H), 4.13 (d, 2H, J=6.6 Hz), 4.88 (s, 2H), 7.22-7.24 (m, 2H), 7.36-7.38 (m, 1H), 7.66-7.69 (m, 1H).

후처리

  1. temperatureThen it was cooled to room temperature
  2. customquenched with saturated NaHCO3 (15 mL)
  3. customthe phases were separated
  4. washThe aqueous phase was washed with CH2Cl2 (3×20 mL)
  5. washThen the combined organic layers were washed with brine (2×30 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried in vacuo
  10. customto afford a dark brown oil
  11. customPurification by flash column chromatography on silica gel using 2% CH3OH/CH2Cl2

출처 및 근거

ORD 기록
ord-233b25b5575e4ac694bb3ab0eed68b41
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354932B2

연결된 노트

불러오는 중…