N,N-Dimethylglycine → {4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}methanol

HRID 230676

반응식

HRID 230676 반응식
I[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[NH:14][N:13]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[F:22][C:11]([F:10])([F:21])[C:12]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]([C:2]2[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=2)[N:13]=1

참가 물질

7

반응물 4

HCID 673N,N-DimethylglycineHCID 11430Potassium CarbonateHCID 290124-Iodobenzyl alcoholHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

생성물 1

HCID 24825810{4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}methanol수율 86%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

A mixture of 4-iodobenzylalcohol (1.23 g, 5.25 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (950 mg, 5 mmol), copper (I) iodide (10 mol %, 95 mg, 0.5 mmol), N,N-dimethylglycine (20 mol %, 103 mg, 1 mmol) and potassium carbonate (1.45 g, 10.5 mmol) in dimethylsulfoxide (30 ml) was stirred at 130° C. in an oil bath for 23 h. The reaction mix was cooled and partitioned between dichloromethane (30 ml) and brine (150 ml). The organic layer was removed filtered and the solvent removed under reduced pressure. The resulting product was purified by flash column chromatography on a Biotage 40+M column eluting from 0-60% ethyl acetate in pentane to give the title compound as a yellow oil (1.27 g, 86%).

후처리

  1. additionThe reaction mix
  2. temperaturewas cooled
  3. custompartitioned between dichloromethane (30 ml) and brine (150 ml)
  4. customThe organic layer was removed
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe resulting product was purified by flash column chromatography on a Biotage 40+M column
  8. washeluting from 0-60% ethyl acetate in pentane

출처 및 근거

ORD 기록
ord-71647b96e3d44e71b10c96f979a56248
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566735B2

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