Cesium carbonate → HCID 66287435, compound

HRID 2202064Notes

Reaction equation

HRID 2202064 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1.Cl.[O:13]1[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 820890Methyl 4-ChloropicolinateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 441186934-Aminotetrahydropyran hydrochloride

Product 1

HCID 66287435HCID 66287435, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of compound methyl 4-chloropicolinate (100 mg, 0.59 mmol), tetrahydro-2H-pyran-4-amine hydrochloride (121 mg, 0.88 mmol), Cs2CO3 (762 mg, 2.34 mmol), Pd2(dba)3 (54 mg, 0.059 mmol) and XPhos (28 mg, 0.06 mmol) in toluene (10 mL) was stirred and heated at 110° C. under N2 for 16 h. The catalyst was filtered and the filtrate was washed with EA, concentrated in vacuo and the residue was purified by prep-TLC to give the title product (50 mg, Yield 36.2%). LCMS (m/z): 237.2 (M+1).

Workup

  1. filtrationThe catalyst was filtered
  2. washthe filtrate was washed with EA
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-249018f2617443548d238c23a4aa1c01
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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