Triethylamine → ethyl 8-(2-Ethyl-6-methylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-carboxylate

HRID 1166169ノート

反応式

HRID 1166169 の反応式
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:17]([C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH:21]=O)[CH3:18].C([BH3-])#N.[Na+].C(N(CC)CC)C>CO.[Cl-].[Zn+2].[Cl-]>[CH2:17]([C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)[CH3:18]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 22672637Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylateHCID 229974692-Ethyl-6-methylbenzaldehyde

生成物 1

HCID 22997468ethyl 8-(2-Ethyl-6-methylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-carboxylate収率 8.1%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒2 回

実験手順

To a stirred mixture of ethyl 8-amino-3-methylimidazo[1,2-a]pyridin-2-carboxylate (1.53 g, 7.0 mmol) in methanol (25 ml) were added 2-ethyl-6-methylbenzaldehyde (1.1 g, 7.1 mmol), zinc(II)chloride (1.1 g, 8.0 mmol) in methanol (10 ml) and sodium cyanoborohydride (0.5 g, 8.0 mmol). The reaction mixture was refluxed for 4 h. and then stirred at room temperature for 20 h. Triethylamine (2.5 ml) was added and the mixture was stirred for 30 min. and evaporated under reduced pressure. Purification of the residue by column chromatography twice on silica gel using 1) methylene chloride:methanol (95:5) 2) heptane:isopropyl ether (1:5) as eluent gave 0.2 g (8%) of the title compound.

後処理

  1. temperatureThe reaction mixture was refluxed for 4 h.
  2. stirringthe mixture was stirred for 30 min.
  3. customevaporated under reduced pressure
  4. customPurification of the residue by column chromatography twice on silica gel using 1) methylene chloride:methanol (95:5) 2) heptane:isopropyl ether (1:5) as eluent

出典と根拠

ORDレコード
ord-80da9f086b924dc391ffbf26a527ba0c
出典データセット
uspto-grants-2003_09
特許番号
US06613775B1

反応ノート

読み込み中…