Ethanol → 3-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

HRID 475141

반응식

HRID 475141 반응식
I[C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C[CH2:38][OH:39]>[Cu]I>[CH3:38][O:39][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 71272550HCID 71272550, 화합물

생성물 1

HCID 712722393-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile수율 35.7%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

반응 조건

온도
90 °C

실험 절차

A mixture of 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (50 mg, 0.142 mmol), CuI (13.5 g 0.071 mmol), CsCO3 (2.7 mg, 0.0142 mmol), and 3,4,7,8-tetramethyl-1,10-phenanthroline (0.0142 mg, 3.5 mmol) in EtOH (0.5 mL) under nitrogen in a sealed vial was heated to 90° C. in a microwave oven for 100 min. The reaction mixture was quenched with water and extracted with EtOAc. The extract was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc to afford 3-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as white solid (13 mg, 35.7%). MS (ESI): m/z=258 [M+1]+.

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 chromatography
  7. washeluting with petroleum ether

출처 및 근거

ORD 기록
ord-e03f189af0724914bfbf36403b22ab3f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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