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

HRID 1270329ノート

反応式

HRID 1270329 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-041d7e21e25648c48d8a2f3306ffb0a7
出典データセット
uspto-grants-2007_04
特許番号
US07202250B2

反応ノート

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