Ethyl Acetate → HCID 58853204、化合物

HRID 659980ノート

反応式

HRID 659980 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](C)[CH:14]=2)[CH2:10][CH2:11][CH3:12])[CH:5]=[N:4][CH:3]=1.[CH3:20]C1(C)C(C)(C)OB(C2C=CC(O)=CC=2)O1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)CC.C1(C)C=CC=CC=1.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>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:13]2[CH:14]=[CH:15][C:16]([CH3:20])=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH3:12])[CH:5]=[N:4][CH:3]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 58853220HCID 58853220、化合物

生成物 1

HCID 58853204HCID 58853204、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 22495535HCID 22495535、化合物溶媒

実験手順

Under a nitrogen atmosphere a mixture of 6-chloro-N-[1-(3-methylphenyl)butyl]pyrazin-2-amine (0.21 g, 0.76 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.23 g, 91 mmol), tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.08 mmol) in toluene-n-propanol (4 mL, 3:1) was treated with 2M aqueous sodium carbonate solution (0.4 mL, 0.84 mmol). The resulting mixture was stirred vigorously whilst being heated under reflux for 22 hours. Once cool ethyl acetate was added and the mixture dried (MgSO4) and filtered. Removal of solvent in vacuo then yielded crude product, which was purified by column chromatography using dichloromethane:diethyl ether (90:10) as eluent to furnish (0.165 g, 60%).

後処理

  1. temperaturewhilst being heated
  2. temperatureunder reflux for 22 hours
  3. dry with materialthe mixture dried (MgSO4)
  4. filtrationfiltered
  5. customRemoval of solvent in vacuo
  6. customthen yielded crude product, which
  7. customwas purified by column chromatography
  8. customto furnish (0.165 g, 60%)

出典と根拠

ORDレコード
ord-6f8a1a40789245b195a889039a5c3397
出典データセット
uspto-grants-2011_12
特許番号
US08084456B2

反応ノート

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