3-Nitrophenylboronic Acid → N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

HRID 17272

反応式

HRID 17272 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.[N+:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].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>[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]=1[C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:29]=1

参加物

6

反応物 3

HCID 16773-Nitrophenylboronic AcidHCID 62657Potassium Phosphate, TribasicHCID 86630795N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

生成物 1

HCID 86630799N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide収率 68%

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) (965 mg, 2.14 mmol), 3-nitrophenylboronic acid (375 mg, 2.25 mmol), tripotassium phosphate (74-85%, 1.23 g, 4.28 mmol) and tetrakis(triphenylphosphine)palladium(0) (247 mg, 0.214 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→4:1) to obtain the entitled compound (645 mg, 68%) as a pale yellow 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→4:1)

出典と根拠

ORDレコード
ord-46e9cb6bc03c480192ede021d4b673a4
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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