Ethyl (chloroformyl)acetate → Ethyl 7-iodo-6-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1748199ノート

反応式

HRID 1748199 の反応式
[I:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1.C(=O)(O)[O-].[Na+].Cl[CH:16]([CH:22]=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(COC)OC.ClCCl>[I:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][N:9]=[C:4]2[CH:3]=1

参加物

6

反応物 3

HCID 118030Ethyl (chloroformyl)acetateHCID 516892Sodium BicarbonateHCID 667478634-Iodo-5-methylpyridin-2-amine

生成物 1

HCID 67985150Ethyl 7-iodo-6-methylimidazo[1,2-a]pyridine-3-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
100 °C

実験手順

To a suspension of 4-iodo-5-methylpyridin-2-amine (I-28A) (1.55 g. 6.6 mmol), sodium bicarbonate (0.67 g, 7.9 mmol) in dry dimethoxyethane (10 mL) at room temperature, ethyl 2-chloro-3-oxopropanoate (1 g, 6.41 mmol) in dimethoxyethane (1 mL) was added dropwise. The reaction mixture was heated to 100° C. for 1 h and then cooled to room temperature and diluted with dichloromethane (50 mL). The organic layer was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The brown crude oil was purified by silica gel chromatography with a gradient of 0-15% ethyl acetate/hexanes to yield ethyl 7-iodo-6-methylimidazo[1,2-a]pyridine-3-carboxylate (I-28B) as light tan solid. 1H-NMR (400 MHz, DMSO) δ 9.11 (s, 1H), 8.41 (s, 1H), 8.22 (s, 1H), 4.36 (q, J=7.2 Hz, 2H), 2.42 (s, 3H), 1.37 (t, J=7.2 Hz, 3H). MS m/z 331.0 (M+1).

後処理

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe brown crude oil was purified by silica gel chromatography with a gradient of 0-15% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-5549f69cc4a043b0b40e6aa6599c2f50
出典データセット
uspto-grants-2015_10
特許番号
US09150568B2

反応ノート

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