Cesium carbonate → HCID 66287435, compound

HRID 880321Notes

Reaction equation

HRID 880321 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-f5a65e25525847a9b8c092c255dcc940
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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