Sodium Carbonate → HCID 68631622, compound

HRID 2196433Notes

Reaction equation

HRID 2196433 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.[C:12]([O:16][CH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(COC)OC>[C:12]([O:16][CH2:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=2)[CH:21]=[CH:20][CH:19]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2930972-Acetamido-5-bromopyridineHCID 37738083-tert-Butoxymethylphenylboronic acid

Product 1

HCID 68631622HCID 68631622, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon stream, 1.0 g of N-(5-bromopyridin-2-yl)acetamide, 967 mg of 3-(tert-butoxymethyl)phenylboronic acid and 269 mg of tetrakis(triphenylphosphine)-palladium are placed in a round-bottomed flask containing 30 ml of dimethoxyethane and 15 ml of a 2M solution of sodium carbonate degassed beforehand. The mixture is heated at 90° C. for 15 hours. After cooling, the reaction mixture is concentrated under reduced pressure. The residue is taken up between dichloromethane and water, the organic phase is separated and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. The residue is then purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. The solid obtained is triturated with diethyl ether, recovered by filtration and then dried. 1.0 g of compound is obtained.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customthe organic phase is separated
  4. dry with materialdried over sodium sulfate
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is then purified by silica gel chromatography, elution
  7. customThe solid obtained
  8. customis triturated with diethyl ether
  9. filtrationrecovered by filtration
  10. customdried

Sources & evidence

ORD record
ord-587136aecea7428f8a44d1de29fdf82b
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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