Sodium Carbonate → HCID 44554829, compound

HRID 220008Notes

Reaction equation

HRID 220008 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[N+:4]([O-:17])[CH:3]=1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C.O>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>[C:11]1([CH2:10][CH2:9][NH:8][C:6]2[CH:5]=[N+:4]([O-:17])[CH:3]=[C:2]([C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[N:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 19096565Water ethanolHCID 44554831HCID 44554831, compound

Product 1

HCID 44554829HCID 44554829, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

A mixture containing 0.250 g (1.0 mmol) of 6-chloro-N-(2-phenylethyl)pyrazin-2-amine 4-oxide, 0.296 g (2.40 mmol) of 4-pyridine boronic acid, 0.60 mL (1.2 mmol) of a 2M solution of sodium carbonate in water and 0.116 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium (0) in 5 mL of a mixture of ethanol/water in the proportions 5/1 was stirred under reflux for 16 h. Cooled water was added and the mixture extracted with dichloromethane, dried over sodium sulfate and evaporated to dryness. The residue obtained was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/diethylamine in the proportions 98/2/0.2 to give after trituration with diethyl ether 0.058 g (20%) of pure product as a yellow solid.

Workup

  1. temperatureunder reflux for 16 h
  2. extractionthe mixture extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue obtained
  6. customwas purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/diethylamine in the proportions 98/2/0.2
  7. customto give after trituration with diethyl ether 0.058 g (20%) of pure product as a yellow solid

Sources & evidence

ORD record
ord-443013a239db40b2868d40ac5d3117f2
Source dataset
uspto-grants-2012_06
Patent number
US08202874B2

Reaction notes

Loading…