Sodium Carbonate → HCID 118497029, compound

HRID 522096Notes

Reaction equation

HRID 522096 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([NH:20][CH:21]2[CH2:23][CH2:22]2)=[O:19])[CH:8]=1)=[O:5].O1CCOCC1.Br[C:44]1[C:49]([F:50])=[CH:48][CH:47]=[CH:46][N:45]=1.C([O-])([O-])=O.[Na+].[Na+]>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:27]=[CH:26][C:25]([C:44]2[C:49]([F:50])=[CH:48][CH:47]=[CH:46][N:45]=2)=[CH:24][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=[C:9]([C:18]([NH:20][CH:21]2[CH2:23][CH2:22]2)=[O:19])[CH:8]=1)=[O:5]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27628032-Bromo-3-fluoropyridineHCID 123184206HCID 123184206, compound

Product 1

HCID 118497029HCID 118497029, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To the solution of 5-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-N-cyclopropyl-1-phenyl-1H-pyrazole-3-carboxamide in dioxane (Preparation 10, 0.63 mmol, 15 mL) was added 2-bromo-3-fluoropyridine (58 mg, 0.33 mmol), Na2CO3 (46.6 mg, 0.44 mmol) in water (1 mL) and Pd(dppf)Cl2 (9 mg, 0.01 mmol). The reaction was degassed with nitrogen for 30 minutes and heated to 110° C. for 17 hours. The reaction was cooled and concentrated in vacuo. The residue was eluted through a small plug of silica with EtOAc followed by reverse phase column chromatography eluting with 3-60% MeCN (containing 0.1% NH4OH) in water (containing 0.1% NH4OH) to afford the title compound (20 mg, 19%).

Workup

  1. customThe reaction was degassed with nitrogen for 30 minutes
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. washThe residue was eluted through a small plug of silica with EtOAc
  5. washeluting with 3-60% MeCN (containing 0.1% NH4OH) in water (containing 0.1% NH4OH)

Sources & evidence

ORD record
ord-fc85a6a1ea724ef384e60fb6673e5d94
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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