Potassium Carbonate → HCID 118456284, compound

HRID 522124Notes

Reaction equation

HRID 522124 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:22](B2OC(C)(C)C(C)(C)O2)=[CH:21][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]([NH2:20])=[O:19])[CH:8]=1)=[O:5].Cl[C:35]1[N:40]=[C:39]([NH2:41])[CH:38]=[CH:37][C:36]=1[F:42].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:41][C:39]1[N:40]=[C:35]([C:22]2[CH:23]=[CH:24][C:2]([Cl:1])=[C:3]([CH:21]=2)[C:4]([NH:6][C:7]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=[C:9]([C:18]([NH2:20])=[O:19])[CH:8]=2)=[O:5])[C:36]([F:42])=[CH:37][CH:38]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 132907526-Chloro-5-fluoro-2-pyridinamineHCID 124035547HCID 124035547, compound

Product 1

HCID 118456284HCID 118456284, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxamide (Preparation 3, 50 mg, 0.11 mmol), 6-chloro-5-fluoropyridin-2-amine (47 mg, 0.32 mmol), tetrakis(triphenylphosphine)palladium (12 mg, 0.01 mmol) and potassium carbonate (30 mg, 0.21 mmol) in dioxane (1.5 mL) and water (1.5 mL) was heated at 110° C. under microwave irradiation for 1 hour. The reaction was poured into water (25 mL) and extracted with EtOAc (2×25 mL). The organic layer was washed with brine (10 mL), dried over magnesium sulphate and concentrated in vacuo.

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd6c1b6fa84c49ba83b32f8e319b7a8a
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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