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

HRID 230676

反応式

HRID 230676 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-71647b96e3d44e71b10c96f979a56248
出典データセット
uspto-grants-2009_07
特許番号
US07566735B2

関連ノート

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