Potassium Phosphate, Tribasic → 2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile

HRID 1028958ノート

反応式

HRID 1028958 の反応式
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Br[C:44]1[C:51]([CH3:52])=[CH:50][CH:49]=[CH:48][C:45]=1[C:46]#[N:47].[O:53]1[CH2:58][CH2:57][N:56]([C:59]2[C:60]([NH2:78])=[N:61][C:62]3[C:67]([CH:68]=2)=[CH:66][C:65](B2OC(C)(C)C(C)(C)O2)=[CH:64][CH:63]=3)[CH2:55][CH2:54]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[NH2:78][C:60]1[C:59]([N:56]2[CH2:57][CH2:58][O:53][CH2:54][CH2:55]2)=[CH:68][C:67]2[C:62](=[CH:63][CH:64]=[C:65]([C:44]3[C:51]([CH3:52])=[CH:50][CH:49]=[CH:48][C:45]=3[C:46]#[N:47])[CH:66]=2)[N:61]=1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 154691152-Bromo-3-methylbenzonitrileHCID 673479953-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

生成物 1

HCID 673450552-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
140 °C

実験手順

To a mixture of potassium phosphate (5.98 g, 28.2 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.54 g, 1.13 mmol), Pd2(dba)3 (0.26 g, 0.28 mmol), 2-bromo-3-methylbenzonitrile (2.21 g, 11.26 mmol) and 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (2.00 g, 5.63 mmol, prepared as in Example 2, Step 1-2) was added dioxane (50.0 mL) and water (25.0 mL). The mixture was heated to 140° C. for 10 min. The reaction mixture was allowed to cool to RT, filtered and then partitioned between EtOAc and water. The organic layer was washed with water and brine, and concentrated. The residue was diluted with EtOAc and then filtered. The solid was dried in air to afford 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile as a light brown solid.

後処理

  1. temperatureto cool to RT
  2. filtrationfiltered
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed with water and brine
  5. concentrationconcentrated
  6. additionThe residue was diluted with EtOAc
  7. filtrationfiltered
  8. customThe solid was dried in air

出典と根拠

ORDレコード
ord-7f6f23c9a4ae497b955691427325cfcf
出典データセット
uspto-grants-2014_05
特許番号
US08735384B2

反応ノート

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