Dichloromethane → HCID 86688292, compound

HRID 334070Notes

Reaction equation

HRID 334070 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[N:22]=[CH:21][N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)[N:19]=3)=[O:17])[C:12]([CH3:31])([CH3:30])[CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[O:32]1[CH2:37][CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH2:34][CH2:33]1.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CO>[Cl:29][C:25]1[CH:24]=[C:23]([N:20]2[CH:21]=[N:22][C:18]([C:16]([N:13]3[CH2:14][CH2:15][N:10]([C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([C:35]5[CH2:36][CH2:37][O:32][CH2:33][CH:34]=5)[N:7]=4)=[O:9])[CH2:11][C:12]3([CH3:31])[CH3:30])=[O:17])=[N:19]2)[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 86688291HCID 86688291, compound

Product 1

HCID 86688292HCID 86688292, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 500 mg (0.10 mmol) [4-(6-bromo-pyridine-2-carbonyl)-2,2-dimethyl-piperazin-1-yl]-[1-(3-chloro-phenyl)-1H-[1,2,4]triazol-3-yl]-methanone, 28 mg (0.13 mmol) 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester, 16 mg (0.020 mmol) [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with DCM (1:1) and 0.10 mL 5M aqueous potassium carbonate solution in 1.0 mL dioxane and 0.50 mL MeOH was stirred at 140° C. for 15 min under microwave irradiation. The reaction mixture was filtered through Alox (alkaline) and purified by HPLC.

Workup

  1. filtrationThe reaction mixture was filtered through Alox (alkaline)
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-da197f05a6d04342ac9d7f26743492d9
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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