4-Methylmorpholine → 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine

HRID 885940Notes

Reaction equation

HRID 885940 reaction equation
[NH:1]1[CH:5]=[C:4]([B:6]2[O:14][C:11]([CH3:13])([CH3:12])[C:8]([CH3:10])([CH3:9])[O:7]2)[CH:3]=[N:2]1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Cl)[CH:16]=1.CN1CCOCC1>CN(C=O)C>[CH3:12][C:11]1([CH3:13])[C:8]([CH3:9])([CH3:10])[O:7][B:6]([C:4]2[CH:3]=[N:2][N:1]([CH2:21][C:17]3[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=3)[CH:5]=2)[O:14]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 183583-(Chloromethyl)pyridineHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 179991853-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The title compound was prepared from pyrazole-4-boronic acid pinacol ester and 3-picolyl chloride (prepared from the hydrochloride salt using a pre-swelled suspension of morpholinomethyl polystyrene in DMF) according to Method AC (heating to 100° C. under microwave irradiation for 2 h) and was isolated as a brown oil (71%). LCMS (ES+) 286 (M+H)+, RT 1.98 minutes (Method 1).

Sources & evidence

ORD record
ord-72f2807011534528a47a610da987e871
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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