Dichloromethane → HCID 59377435, compound

HRID 386652Notes

Reaction equation

HRID 386652 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1Br.[CH2:15](Cl)Cl.C([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[CH3:15]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 59377425HCID 59377425, compound

Product 1

HCID 59377435HCID 59377435, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To 7-amino-6-bromo-1-methyl-3,4-dihydro-1H-quinolin-2-one 1 (57 mg, 0.615 mmol) dissolved in 4 ml degassed dioxane was added 50 mg (0.0615 mmol) PdCl2dppf.CH2Cl2, K2CO3 (255 mg 1.845 mmol), 400 ul H2O, and 86 ul (0.615 mmol) trimethylboroxine. The mixture was heated to 110° C. and stirred for 12 hours, then cooled and partitioned between ethyl acetate and brine. The organic layer was dried over MgSO4 filtered and concentrated under reduced pressure. Purification by column chromatography, eluting with 75% ethyl acetate/hexanes, provided 75 mg of 7-amino-1,6-dimethyl-3,4-dihydro-1H-quinolin-2-one.

Workup

  1. customdegassed dioxane
  2. temperaturecooled
  3. custompartitioned between ethyl acetate and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography
  8. washeluting with 75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-503ad8051d7542d28b5600f4a00429f6
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

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