Acetone → 4-(4-iodo-1H-pyrazol-1-yl)cyclohexanone

HRID 511338노트

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HRID 511338 반응식
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:15]=[C:14]([I:16])[CH:13]=[N:12]3)[CH2:7][CH2:6]2)[O:4]CC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC(C)=O>O>[I:16][C:14]1[CH:13]=[N:12][N:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH:15]=1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 595411251-(1,4-Dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole2회

생성물 1

HCID 595411654-(4-iodo-1H-pyrazol-1-yl)cyclohexanone

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

A mixture of 1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole (Compound 137F, 3.0 g, 8.9 mmol), pyridinium p-toluenesulfonate (4.5 g, 17.9 mmol), acetone (100 mL) and H2O (100 mL) was heated at 60° C. overnight. Work-up: Solvent was evaporated and the residue was extracted with EtOAc (3×60 mL). The combined extracts were washed with water (3×50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound as white solid. It was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=2.23-2.63 (m, 8 H), 4.57-4.64 (m, 1 H), 7.51 (s, 1 H), 7.54 (s, 1 H). MS (ES+): m/z=291.09 (100). HPLC: tR=2.79 min (polar—5 min, ZQ3).

후처리

  1. customSolvent was evaporated
  2. extractionthe residue was extracted with EtOAc (3×60 mL)
  3. washThe combined extracts were washed with water (3×50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-80f03c31f257450fb7fdd2f7858debbb
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096624B2

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