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Benzyl Alcohol → HCID 178477827, 화합물

HRID 2208998
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HRID 2208998 반응식
Cl[C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([Cl:11])[N:3]=1.[OH-].[Na+].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([Cl:11])[N:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
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참가 물질

4

반응물 3

HCID 244Benzyl AlcoholHCID 14798Sodium HydroxideHCID 178477826HCID 178477826, 화합물

생성물 1

HCID 178477827HCID 178477827, 화합물

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온도
150 °C

실험 절차

To a solution of 4,6-dichloro-3H-imidazo[4,5-c]pyridine (2.00 g, 10.6 mmol) in BnOH (23 mL) was added powdered NaOH (1.28 g, 31.9 mmol) and the reaction was heated to 150° C. overnight. The benzyl alcohol was removed by vacuum distillation, and the residue was suspended in water (15 mL) and AcOH (3 mL) was added to bring the pH to ˜7. The aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organics were dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (1:1 hex EtOAc-->EtOAc/10% MeOH) to afford 4-(benzyloxy)-6-chloro-3H-imidazo[4,5-c]pyridine 2.24.

후처리

  1. customThe benzyl alcohol was removed by vacuum distillation
  2. additionAcOH (3 mL) was added
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (1:1 hex EtOAc-->EtOAc/10% MeOH)

출처 및 근거

ORD 기록
ord-36a824effd12405d80fba73d31855217
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376441B2

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