Morpholine → HCID 67338283, compound

HRID 1909122Notes

Reaction equation

HRID 1909122 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[F:19])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O.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]>[F:19][C:13]1[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]=1[C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86657029HCID 86657029, compound

Product 1

HCID 67338283HCID 67338283, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-chloro-6-(2-fluoro-4-methylphenyl)isonicotinate (0.26 g, 0.94 mmol) in DMA (4 mL) were added morpholine (0.10 mL, 1.17 mmol), tris(dibenzylideneacetone)dipalladium(0) (21.4 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (33.5 mg, 0.07 mmol) and cesium carbonate (0.46 g, 1.41 mmol). The mixture was heated to 80° C. After 18 h, the mixture was filtered. The filtered cake was washed with methanol. The filtrate was concentrated to remove methanol. The solution in DMA was carried onto the next step.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filtered cake was washed with methanol
  3. concentrationThe filtrate was concentrated
  4. customto remove methanol

Sources & evidence

ORD record
ord-98c51c16fb7d42119107e63cf2c0b0d7
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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