Sodium Carbonate → HCID 68008520, compound

HRID 1528110Notes

Reaction equation

HRID 1528110 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[O:9]1[CH2:14][CH:13]=[C:12](B2OC(C)(C)C(C)(C)O2)[CH2:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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>[O:9]1[CH2:10][CH:11]=[C:12]([C:2]2[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 885792-Pyridinamine, 5-iodo-HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Product 1

HCID 68008520HCID 68008520, compoundYield 110.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

0.220 g of 5-iodopyridin-2-amine (1.0 mmol), 0.315 g of 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.50 mmol), 0.116 g of tetrakis(triphenylphosphine)palladium(0) (0.100 mmol) and 2.25 ml of a 2M sodium carbonate solution (4.50 mmol) were dissolved/suspended in 8.6 ml of DMF in a microwave vessel, flushed with vacuum/argon, and subsequently heated in the microwave for 20 min at 120° C. HPLC/MSD indicated almost complete formation of the desired product. The solvent was evaporated under reduced pressure, 2M HCl was added to the residue and the mixture extracted three times with DCM. To the acidic water phase 2M NaOH was added up to pH 9 and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate solutions were washed once with brine, dried over sodium sulfate and the solvent removed under reduced pressure. 195 mg of the desired product were obtained as yellow powder (yield: quant.). The quite pure raw material (about 90%) was used without further purification in the next step.

Workup

  1. customflushed with vacuum/argon
  2. customThe solvent was evaporated under reduced pressure, 2M HCl
  3. additionwas added to the residue
  4. extractionthe mixture extracted three times with DCM
  5. additionTo the acidic water phase 2M NaOH was added up to pH 9
  6. extractionthe mixture was extracted three times with ethyl acetate
  7. washThe combined ethyl acetate solutions were washed once with brine
  8. dry with materialdried over sodium sulfate
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c85865cd7d0c44f08b736de69875c9ce
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

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