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

HRID 2383931ノート

反応式

HRID 2383931 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-c2f7d6b69230422db0015242029973d8
出典データセット
uspto-grants-2012_09
特許番号
US08263635B2

反応ノート

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