Sodium Iodide → 1,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(phenylmethyl)-

HRID 1713127노트

반응식

HRID 1713127 반응식
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na+].[I-].[BH4-].[Na+]>C(#N)C.CO.O>[CH2:11]([N:7]1[CH2:8][CH2:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 674881,6-NaphthyridineHCID 4311764Sodium borohydride

생성물 1

HCID 30587131,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(phenylmethyl)-

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution 1,6-naphthyridine (2.09 g, 16.05 mmol) in acetonitrile (50.0 ml) is added benzylbromide (3.30 g, 19.27 mmol, 1.2 eq.) and NaI (50.0 mg). The resulting mixture is refluxed under nitrogen overnight. Acetonitrile is evaporated, and the residue is washed with ether (20 ml), and dried in vacuo to give the quaternary salt, which is dissolved in a mixture of MeOH (90 ml) and water (30 ml). To the solution at 0° C. is added sodium borohydride (2.28 g, 96.5 mmol, about 6.0 eq.). The resulting mixture is warmed to rt, and stirred overnight. The organic solvent is evaporated, and the residue is taken up in water (50 ml), extracted with EtOAc (50 ml×3). The combined organic phase is washed with brine, dried over sodium sulfate, and concentrated. The crude product is purified by silica gel chromatography (Hexane/EtOAc 1:1 plus 4% TEA) to give the title compound. MS (+VE) m/z 225.1 (M++1).

후처리

  1. temperatureThe resulting mixture is refluxed under nitrogen overnight
  2. customAcetonitrile is evaporated
  3. washthe residue is washed with ether (20 ml)
  4. customdried in vacuo
  5. customto give the quaternary salt, which
  6. customThe organic solvent is evaporated
  7. extractionextracted with EtOAc (50 ml×3)
  8. washThe combined organic phase is washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe crude product is purified by silica gel chromatography (Hexane/EtOAc 1:1 plus 4% TEA)

출처 및 근거

ORD 기록
ord-9e589606140e492b9e456dba6d9583f6
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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