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

HRID 1028958노트

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HRID 1028958 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
140 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7f6f23c9a4ae497b955691427325cfcf
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735384B2

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