Hexane → N-methoxy-N-methylimidazo[1,2-a]pyridine-7-carboxamide

HRID 341207

反応式

HRID 341207 の反応式
CO[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=[O:4].[CH3:14][N:15](C)[OH:16].[CH3:18][Al](C)C.CCCCCC>C(Cl)Cl>[CH3:18][O:16][N:15]([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 8058HexaneHCID 27970DimethylhydroxylamineHCID 15096964Methyl imidazo(1,2-a)pyridine-7-carboxylateHCID 16682925Trimethylaluminum

生成物 1

HCID 59320928N-methoxy-N-methylimidazo[1,2-a]pyridine-7-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of Imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (0.67 g, 3.83 mmol) and dimethylhydroxylamine (0.93 g, 9.57 mmol) in CH2Cl2 (40 ml) at 0° C. was added 2M trimethylaluminium solution in hexane (3.8 ml, 9.57 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 h, before being cooled back to 0° C. and quenched with ice. The reaction was filtered and liquid fraction partitioned between CH2Cl2/H2O. The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to afford the crude product. The residue was purified by silica column chromatography (0-50% MeOH in Et2O) to afford the product (187 mg). MS: [M+H]+=206.

後処理

  1. temperaturebefore being cooled back to 0° C.
  2. customquenched with ice
  3. filtrationThe reaction was filtered
  4. customliquid fraction partitioned between CH2Cl2/H2O
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customto afford the crude product
  10. customThe residue was purified by silica column chromatography (0-50% MeOH in Et2O)

出典と根拠

ORDレコード
ord-f187bdd8f00149fabc0c4d5902353323
出典データセット
uspto-grants-2014_11
特許番号
US08895745B2

関連ノート

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