Potassium Carbonate → {3-Ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl} [(4-methoxyphenyl)methyl]amine

HRID 889874노트

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HRID 889874 반응식
Br[C:2]1[C:3]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[N:4][C:5]([O:21][CH3:22])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=2[O:19][CH3:20])[N:7]=1.[CH2:33](B(O)O)[CH3:34].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[OH-].[Na+].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>[CH2:33]([C:2]1[C:3]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[N:4][C:5]([O:21][CH3:22])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=2[O:19][CH3:20])[N:7]=1)[CH3:34]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 521157Ethylboronic acidHCID 23594996{3-Bromo-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl} [(4-methoxyphenyl)methyl]amine

생성물 1

HCID 22248943{3-Ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl} [(4-methoxyphenyl)methyl]amine수율 92.8%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 14798Sodium Hydroxide용매

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온도
85 °C

실험 절차

To a stirred solution of {3-bromo-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy) phenyl]pyrazin-2-yl }[(4-methoxyphenyl)methyl]amine (514 mg, 1.0 mmol) and ethylboronic acid (219 mg, 3.0 mmol) in toluene (8 mL) is added tetrakis(triphenylphosphine)palladium(0) (50 mg) and potassium carbonate (2.0 M, 1.0 mL). The mixture is heated to 85° C. for 8 h, cooled to room temperature, diluted with 2.0 M sodium hydroxide and extracted twice with 1:1 hexane-ethyl ether. The combined extracts are dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography, eluting with 20% ether in hexanes to give {3-ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy) phenyl]pyrazin-2-yl }[(4-methoxyphenyl)methyl]amine (430 mg).

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted twice with 1:1 hexane-ethyl ether
  3. dry with materialThe combined extracts are dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography
  7. washeluting with 20% ether in hexanes

출처 및 근거

ORD 기록
ord-b8eb183c88a74c40a93ee9f51e6112ad
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995161B2

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