Potassium Acetate → Cyclopentyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzoate

HRID 1028967Notes

Reaction equation

HRID 1028967 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]([NH2:26])=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13](B2OC(C)(C)C(C)(C)O2)=[CH:12][CH:11]=3)[CH2:3][CH2:2]1.Br[C:28]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:29]=1[C:30]([O:32][CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:31].C([O-])(=O)C.[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.O>[NH2:26][C:8]1[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:28]3[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:29]=3[C:30]([O:32][CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)=[O:31])[CH:14]=2)[N:9]=1

Participants

8

Reactant 4

HCID 517044Potassium AcetateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67325920Cyclopentyl 2-bromo-3-methylbenzoateHCID 673479953-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

Product 1

HCID 53328993Cyclopentyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

3-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.15 g, 0.422 mmol, prepared as Example 2, Step 1-2), cyclopentyl 2-bromo-3-methylbenzoate (0.133 g, 0.470 mmol), potassium acetate (0.079 mL, 1.267 mmol), 2-dicyclohexylphosphino-2′,4′,6′,-triisopropylbiphenyl (0.020 g, 0.042 mmol), palladium(II) acetate (4.74 mg, 0.021 mmol), water (0.3 mL) and ethanol (2 mL) were combined in a microwave vial and heated to 145° C. for 30 min. The crude material was partitioned between water (40 mL) and DCM (50 mL). The organic layer was dried on magnesium sulfate, filtered and concentrated. The crude material was purified by silica chromatography (0-10% methanol in DCM gradient) to give cyclopentyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzoate. MS (ESI, pos. ion) m/z: 432 (M+1).

Workup

  1. customThe crude material was partitioned between water (40 mL) and DCM (50 mL)
  2. customThe organic layer was dried on magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica chromatography (0-10% methanol in DCM gradient)

Sources & evidence

ORD record
ord-dadcf29bce2b4d44a8e9b291984471e2
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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