Potassium Carbonate → HCID 59703428, compound

HRID 421732Notes

Reaction equation

HRID 421732 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[F:7][CH:8]([F:28])[O:9][C:10]1[CH:18]=[CH:17][C:16]([B:19]2[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]2)=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13]>C(#N)C.O>[F:28][CH:8]([F:7])[O:9][C:10]1[CH:18]=[CH:17][C:16]([B:19]2[O:23][C:22]([CH3:24])([CH3:25])[C:21]([CH3:27])([CH3:26])[O:20]2)=[CH:15][C:11]=1[C:12]([NH:14][CH3:1])=[O:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59703486HCID 59703486, compound

Product 1

HCID 59703428HCID 59703428, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of the appropriate chloro-substrate (1 equiv), potassium carbonate (3.0 equiv), 2-difluoromethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (1.1 equiv) and tetrakis(triphenylphosphine) palladium0 (0.05 equiv) in acetonitrile/water (0.1 M of chloro-substrate) was stirred at 100° C. for 2 hours. Upon completion the reaction mixture was partitioned between water and CH2Cl2 and extracted with CH2Cl2. Combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by preparative HPLC to give the desired product.

Workup

  1. customUpon completion the reaction mixture was partitioned between water and CH2Cl2
  2. extractionextracted with CH2Cl2
  3. washCombined organic phases were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cccc9b1f3570435eabacb923063a21b9
Source dataset
uspto-grants-2012_01
Patent number
US08101602B2

Reaction notes

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