Cesium carbonate → 1-(1,4-Dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole

HRID 1505682ノート

反応式

HRID 1505682 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[I:22][C:23]1[CH:24]=[N:25][NH:26][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O.CCOC(C)=O>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([N:25]3[CH:24]=[C:23]([I:22])[CH:27]=[N:26]3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

生成物 1

HCID 595411251-(1,4-Dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole収率 136.1%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A mixture of Toluene-4-sulfonic acid 1,4-dioxa-spiro[4.5]dec-8-yl ester (4.47 g; 13.9 mmol; 1.0 eq.), 4-Iodo-1H-pyrazole (2.69 g; 13.9 mmol; 1.0 eq.) and cesium carbonate (6.78 g; 20.8 mmol; 1.5 eq.) was heated in DMA (50.0 mL) at 100° C. for 3 h. It was then allowed to cool to RT, diluted with EtOAc and washed with water and brine. Aqueous phases were back-extracted with EtOAc. Combined organic phases were finally dried over sodium sulfate, filtered and concentrated to give 6.32 g of a yellow oil. Recrystallisation in iPrOH afforded the title compound as a white powder (2.81 g, 61%). HPLC (Condition A): Rt 3.46 min (purity 100%). MS (ESI+): 335.1.

後処理

  1. washwashed with water and brine
  2. extractionAqueous phases were back-extracted with EtOAc
  3. dry with materialCombined organic phases were finally dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-c3dc29640f934c5580b778f3a6777dd7
出典データセット
uspto-grants-2015_12
特許番号
US09216991B2

反応ノート

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