Potassium Carbonate → 2-amino-N,N-dimethyl-5-[8-methyl-4-(4-pyridinyl)-6-quinolinyl]-3-pyridinesulfonamide

HRID 1096781

反応式

HRID 1096781 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[NH2:37][C:38]1[C:43]([S:44]([N:47]([CH3:49])[CH3:48])(=[O:46])=[O:45])=[CH:42][C:41](Br)=[CH:40][N:39]=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:65]2[CH:70]=[CH:69][N:68]=[CH:67][CH:66]=2)O1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[NH2:37][C:38]1[C:43]([S:44]([N:47]([CH3:49])[CH3:48])(=[O:46])=[O:45])=[CH:42][C:41]([C:2]2[CH:3]=[C:4]3[C:9](=[C:10]([CH3:12])[CH:11]=2)[N:8]=[CH:7][CH:6]=[C:5]3[C:65]2[CH:70]=[CH:69][N:68]=[CH:67][CH:66]=2)=[CH:40][N:39]=1

参加物

10

反応物 6

HCID 11430Potassium Carbonate2 回HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 435319436-Bromo-4-chloro-8-methylquinolineHCID 523351532-amino-5-bromo-N,N-dimethylpyridine-3-sulfonamide

生成物 1

HCID 598600222-amino-N,N-dimethyl-5-[8-methyl-4-(4-pyridinyl)-6-quinolinyl]-3-pyridinesulfonamide収率 28%

試薬・触媒・溶媒 3

HCID 53485975CID 53485975触媒2 回HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒2 回

実験手順

A mixture of 6-bromo-4-chloro-8-methylquinoline (0.300 g, 1.170 mmol), bis(pinacolato)diboron (0.297 g, 1.170 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.029 g, 0.035 mmol), and solid anhydrous potassium acetate (0.459 g, 4.676 mmol) in dry 1,4-dioxane (8 mL) was heated at reflux for 70 minutes. The oil bath was temporarily removed and to the reaction was added 2-amino-5-bromo-N,N-dimethyl-3-pyridinesulfonamide (0.327 g, 1.17 mmol), dichloro [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.047 g, 0.058 mmol), and 2 M aqueous potassium carbonate (0.646 g, 4.676 mmol, 2.34 mL). The reaction was heated at reflux for 80 minutes. The oil bath was temporarily removed and to the reaction was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.240 g, 1.17 mmol), dichloro [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.047 g, 0.058 mmol), 2 M aqueous potassium carbonate (0.485 g, 3.51 mmol, 1.76 mL), and 1,4-dioxane (6 mL). The reaction was heated at reflux for 17 h and concentrated in vacuo. The residue was triturated with 10% MeOH:EtOAc (45 mL), filtered through filter paper, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (7% MeOH:EtOAc) to give the title compound (0.135 g, 28%) as a yellow powder. MS(ES)+ m/e 420 [M+H].

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 70 minutes
  3. customThe oil bath was temporarily removed and to the reaction
  4. temperatureThe reaction was heated
  5. temperatureat reflux for 80 minutes
  6. customThe oil bath was temporarily removed and to the reaction
  7. temperatureThe reaction was heated
  8. temperatureat reflux for 17 h
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with 10% MeOH
  11. filtrationEtOAc (45 mL), filtered
  12. filtrationthrough filter paper
  13. concentrationthe filtrate was concentrated in vacuo
  14. customThe residue was purified by flash chromatography on silica gel (7% MeOH:EtOAc)

出典と根拠

ORDレコード
ord-40cc3201ff9a465bae9cb16e9fc126f8
出典データセット
uspto-grants-2012_03
特許番号
US08138347B2

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