Imidazole → HCID 17946394, 화합물

HRID 991689노트

반응식

HRID 991689 반응식
[CH3:1][Si:2](Cl)([CH3:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[Br:9][C:10]1[C:15]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:13]=[CH:12][N:11]=1.N1C=CN=C1>CN(C=O)C.[OH-].[Na+]>[Br:9][C:10]1[C:15]([O:16][CH2:17][CH2:18][O:19][Si:2]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:7])[CH3:1])=[CH:14][CH:13]=[CH:12][N:11]=1

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 220362632-[(2-Bromopyridin-3-yl)oxy]ethan-1-ol

생성물 1

HCID 17946394HCID 17946394, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 14798Sodium Hydroxide용매

실험 절차

A solution of dimethyl-t-butylsilyl chloride (11.1 g, 74 mmol) in DMF (30 mL) was added to a suspension of 2-bromo-3-(2-hydroxyethoxy)pyridine (15.3 g, 70 mmol; obtained in Example 191, Step 1) and imidazole (10.0 g, 147 mmol) in DMF (30 mL). The reaction mixture was stirred at ambient temperature for 2 h, diluted with 0.5 M aqueous NaOH (0.7 L), and extracted twice with toluene. The combined organic phases were washed once with water, dried (MgSO4), and concentrated. The resulting oil was treated with a mixture of petroleum ether and ethyl acetate (95:5; 50 mL) and an analytical sample of white crystals was collected. The remaining crystals were mixed with the filtrate, the solvent was evaporated and the resulting crude product was used directly in the next step. Solid; yield 18.3 g (78%); mp 81° C. Anal. (C13H22BrNO2Si) C,H,N.

후처리

  1. extractionextracted twice with toluene
  2. washThe combined organic phases were washed once with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionThe resulting oil was treated with a mixture of petroleum ether and ethyl acetate (95:5; 50 mL)
  6. customan analytical sample of white crystals was collected
  7. additionThe remaining crystals were mixed with the filtrate
  8. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-5c3bbee55c5e4c158c789f0364291ce1
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465467B1

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