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

HRID 17273

반응식

HRID 17273 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a5b661dec47f4f8c9684c3c29373a3a7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

연결된 노트

불러오는 중…