Potassium Carbonate → 1-[(6-Ethynylnaphthalen-2-yl)sulfonyl]-4-(4-(pyridin-4-yl)benzoyl]piperazine

HRID 352915

反応式

HRID 352915 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[C:35]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(N(CC)CC)C.CN(C)C=O.C[Si](C#C)(C)C.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.ClCCl>[C:35]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=4)=[CH:24][CH:23]=3)[CH2:19][CH2:20]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2)#[CH:36]

参加物

12

反応物 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 223297051-(6-Bromonaphth-2-ylsulphonyl)4-[4-(4-pyridyl)benzoyl]piperazine

生成物 1

HCID 227095101-[(6-Ethynylnaphthalen-2-yl)sulfonyl]-4-(4-(pyridin-4-yl)benzoyl]piperazine

試薬・触媒・溶媒 8

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒HCID 66111Trimethylsilylacetylene溶媒

実験手順

To a solution of 1-[(6-bromonaphthalen-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)benzoyl]piperazine (310 mg) and triphenylphosphine (455 mg) in tetrahydrofuran (1.0 ml), triethylamine (3.0 ml), N,N-dimethylformamide (1.0 ml), trimethylsilylacetylene (130 ml) and palladium acetate (13.0 mg) were added, followed by heating under reflux for 2 hours. After the reaction mixture was allowed to cool down to room temperature, dichloromethane (15 ml) and water (30 ml) were added to separate the organic layer. The organic layer thus obtained was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (dichloromethane:acetone=3:1), whereby colorless amorphous was obtained. The resulting product was dissolved in methanol (25 ml), followed by the addition of tetrahydrofuran (5.0 ml) and potassium carbonate (300 mg). The resulting mixture was stirred for 30 minutes. Dichloromethane (30 ml) and water (50 ml) were added to the reaction mixture to separate the organic layer. The organic layer thus obtained was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (dichloromethane acetone=4:1), followed by pulverization and washing in a mixed solvent of dichloromethane, acetone and water, whereby the title compound (210 mg, 75%) was obtained.

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. customto separate the organic layer
  4. customThe organic layer thus obtained
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (dichloromethane:acetone=3:1), whereby colorless amorphous
  9. customwas obtained
  10. customto separate the organic layer
  11. customThe organic layer thus obtained
  12. dry with materialwas dried over anhydrous sodium sulfate
  13. distillationdistilled under reduced pressure
  14. customto remove the solvent
  15. customThe residue was purified by chromatography on a silica gel column (dichloromethane acetone=4:1)
  16. washwashing in a mixed solvent of dichloromethane, acetone and water, whereby the title compound (210 mg, 75%)
  17. customwas obtained

出典と根拠

ORDレコード
ord-4c7f3b00435f4f9bbb7267b3d5903221
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

関連ノート

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