3-Nitrophenylboronic Acid → 3-Fluoro-N-(6-methyl-3'-nitrobiphenyl-3-yl)-5-(trifluoromethyl)benzamide

HRID 1894873

반응식

HRID 1894873 반응식
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F:13][C:14]1[CH:15]=[C:16]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22](I)[CH:21]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.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>[F:13][C:14]1[CH:15]=[C:16]([CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1)[C:17]([NH:19][C:20]1[CH:25]=[C:24]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:23]([CH3:26])=[CH:22][CH:21]=1)=[O:18]

참가 물질

8

반응물 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 690440933-fluoro-N-(3-iodo-4-methylphenyl)-5-(trifluoromethyl)benzamide

생성물 1

HCID 690453213-Fluoro-N-(6-methyl-3'-nitrobiphenyl-3-yl)-5-(trifluoromethyl)benzamide수율 97.8%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

(3-Nitrophenyl)boronic acid (1.7 g, 10.0 mmol) was mixed with 3-fluoro-N-(3-iodo-4-methylphenyl)-5-(trifluoromethyl)benzamide (4.30 g, 10.2 mmol) and potassium carbonate (2.5 g, 18 mmol) in toluene (75.00 mL), ethanol (11.00 mL) and water (10.00 mL) and was degassed. To the mixture was added tetrakis(triphenylphosphine)palladium(0) (0.50 g, 0.43 mmol) and the resulting mixture was heated to reflux for 18 hours. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and then concentrated in vacuo. The residue was purified by column chromatography using 20% EtOAc/hexanes to give the product (4.09 g, 96% yield). MS (EI) m/z=419 (M+H).

후처리

  1. customwas degassed
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 18 hours
  4. extractionThe reaction was extracted with ethyl acetate
  5. washthe organic extracts were washed with water, saturated NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-db1f00d1fd534239b44c5a55ef158143
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513270B2

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