Potassium Phosphate, Tribasic → N-(3'-Benzyloxy-2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

HRID 17273

反応式

HRID 17273 の反応式
[Br:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]([C:10]#[N:11])=[C:6]([CH3:9])[C:7]=1I.[CH2:21]([O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([O:28][C:29]1[CH:34]=[C:33]([C:7]2[C:6]([CH3:9])=[C:5]([C:10]#[N:11])[C:4]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[C:3]([O:19][CH3:20])[C:2]=2[Br:1])[CH:32]=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27343133-Benzyloxy-phenylboronic acidHCID 86630795N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

生成物 1

HCID 86630800N-(3'-Benzyloxy-2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide収率 55%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide (I-6) (1.02 g, 2.26 mmol), 3-benzyloxybenzeneboronic acid (541 mg, 2.37 mmol), tripotassium phosphate (74-85%, 1.30 g, 4.52 mmol) and tetrakis(triphenylphosphine)palladium(0) (261 mg, 0.226 mmol) were added to a 50-ml eggplant-type flask, followed by purging with nitrogen. N,N-Dimethylformamide (20 ml) was injected into it with a syringe, followed by stirring at 95° C. for 4 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine, an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was concentrated under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (630 mg, 55%) as a pale brown solid.

後処理

  1. customby purging with nitrogen
  2. customN,N-Dimethylformamide (20 ml) was injected into it with a syringe
  3. temperatureAfter cooling
  4. customthe reaction liquid
  5. washsuccessively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
  6. dry with materialan aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customto obtain a pale brown residue
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

出典と根拠

ORDレコード
ord-a5b661dec47f4f8c9684c3c29373a3a7
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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