Potassium Carbonate → HCID 135547518, compound

HRID 2266957Notes

Reaction equation

HRID 2266957 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3].CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[OH:35])O1.C([O-])([O-])=O.[K+].[K+]>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>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[OH:35])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 58857072HCID 58857072, compound

Product 1

HCID 135547518HCID 135547518, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

6′Chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid isobutyl ester (54 mg, 0.18 mmol), 47.9 mg (0.22 mmol) of 2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol, 3.2 mg (2.7 pmol) of Pd(PPh3)4, 49.2 mg (0.35 mmol) of K2CO3 were charged to a microwave reactor vial. The reaction mixture was heated by microwave irradiation at 120° C. for 15 minutes. The reaction was filtered and purified by reverse phase HPLC (10%-99% CH3CN/H2O), (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to give 33. LCMS: m/z 357.2 (M+H)+ at 3.53 minutes (10%-99% CH3CN/H2O), (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by reverse phase HPLC (10%-99% CH3CN/H2O), (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record
ord-3ccf3b198a614500850b26509659cf7e
Source dataset
uspto-grants-2010_12
Patent number
US07858786B2

Reaction notes

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