Cesium carbonate → HCID 58547859、化合物

HRID 707341ノート

反応式

HRID 707341 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.Cl.[NH:19]1[CH2:22][CH:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:20]1>CN(C)C=O.O>[N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[N:19]1[CH2:22][CH:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:20]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 22101213tert-Butyl azetidin-3-ylcarbamate--hydrogen chloride (1/1)

生成物 1

HCID 58547859HCID 58547859、化合物収率 80%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

Cesium carbonate (4.68 g, 14.4 mmol), 2-chloroquinoline (0.782 g, 4.8 mmol) and tert-butyl azetidin-3-yl-carbamate hydrochloride (1.0 g, 4.8 mmol) were dissolved in dry dimethylformamide (15 mL) and the resulting mixture was heated at 120° C. overnight. The mixture was diluted with water (40 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (30 mL) and brine (30 mL), then dried over sodium sulfate. The organic was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 40% ethyl acetate in petroleum ether) to give tert-butyl (1-(quinolin-2-yl)azetidin-3-yl)-carbamate (1.14 g, 3.84 mmol, 80% yield) as white solid.

後処理

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe organic was evaporated in vacuo
  5. customthe residue was purified by flash column chromatography on silica gel (20% to 40% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-ef82a4e4f62c49918c68d410a37df44d
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

反応ノート

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