Benzyl Bromide → Ammonium Hydroxide

HRID 1421708노트

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HRID 1421708 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:39])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[N:16]=[CH:17][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:19]=3)=[CH:10][N:9]=2)[CH:7]=1.[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CC#N>[NH4+:6].[OH-:39].[CH2:40]([N:16]1[C:15]([CH2:14][C:11]2[CH:12]=[CH:13][C:8]([N:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]3=[O:39])=[N:9][CH:10]=2)=[CH:19][N:18]=[CH:17]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

참가 물질

5

반응물 2

HCID 7498Benzyl BromideHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

생성물 2

HCID 14923Ammonium Hydroxide수율 0.4%HCID 187797495'-(3-Benzyl-3H-imidazol-4-ylmethyl)-5-chloro-[1,2']bipyridinyl-2-one

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

A mixture of 5-chloro-5'-(1-triphenylmethyl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (0.10 g, 0.189 mmol) and benzyl bromide (0.036 g, 0.208 mmol) in CH3CN (1 mL) was heated at 50° C. for 18 h. The solvent was removed in vacuo and the residue was heated to reflux in MeOH (3 mL) for 1 h, then concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (3 mL). The organic layer was removed and the aqueous phase extracted further with CH2Cl2 (2×3 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with CH2Cl2 ; 4% MeOH; 0.4% NH4OH, to give the title compound:

후처리

  1. customThe solvent was removed in vacuo
  2. temperaturethe residue was heated
  3. temperatureto reflux in MeOH (3 mL) for 1 h
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (3 mL)
  6. customThe organic layer was removed
  7. extractionthe aqueous phase extracted further with CH2Cl2 (2×3 mL)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash column chromatography
  12. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-dab4213a3d584a6984116775f83ac430
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077853

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