Ethyl Acetate → 6-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine

HRID 2383931

반응식

HRID 2383931 반응식
Cl[CH2:2][O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7].[OH-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]2[N:21]=[CH:20][NH:19][C:16]2=[N:17][CH:18]=1.C(OC(=O)C)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.CCCCCC>[Br:12][C:13]1[CH:14]=[C:15]2[N:21]=[CH:20][N:19]([CH2:2][O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7])[C:16]2=[N:17][CH:18]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 9115786-Bromo-4H-imidazo[4,5-b]pyridineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

생성물 1

HCID 193582886-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine수율 14.4%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

(2-Chloromethoxy-ethyl)-trimethyl-silane (508.6 mg, 3.0456 mmol), catalytic amount of benzyl triethyl-ammonium chloride and NaOH (203.04 mg, 5.076 mmol) were added to a solution of 6-bromo-3H-imidazo[4,5-b]pyridine (500 mg, 2.538 mmol) in DCM (10 mL) at 0° C. The resulting mixture was stirred room temperature for 6 hours. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was partitioned between DCM and water. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (20% ethylacetate in hexane) afforded 120 mg of the product (14.4% yield).

후처리

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (20% ethylacetate in hexane)

출처 및 근거

ORD 기록
ord-c2f7d6b69230422db0015242029973d8
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263635B2

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