Sodium Carbonate → HCID 86680610, compound

HRID 1497436Notes

Reaction equation

HRID 1497436 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH3:10][NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1.CCO.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>[CH:8]([C:5]1[N:6]=[CH:7][C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:12]([NH:11][CH3:10])=[O:13])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1)=[O:9]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 98775625-Bromopyridine-2-carbaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 86680610HCID 86680610, compoundYield 68.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromopicolinaldehyde (0.25 g, 1.34 mmol) in toluene (6 mL) and EtOH (5 mL) was added (4-(methylcarbamoyl)phenyl)boronic acid (0.36 g, 2.0 mmol), 2M Na2CO3 (2.5 mL, 4.03 mmol) and Pd(PPh3)4 (0.24 g, 0.2 mmol) under argon. The mixture was degassed, heated to 100° C., and stirred for 1 h. After completion of the reaction by monitoring with TLC (80% EtOAc\hexane), the resulting mixture was filtered using Celite® reagent. The filtrate was separated, concentrated, extracted with EtOAc (2×100 mL), washed with water (100 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel 100-200μ) using 60% ethyl acetate in hexane and isolated as a yellow solid (0.22 g, 62% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.0 (s, 1H), 9.20 (s, 1H), 8.53 (s, 2H), 8.39 (d, 2H), 7.9 (m, 3H); LC-MS: m/z 241.4 [M+H]+.

Workup

  1. customThe mixture was degassed
  2. customAfter completion of the reaction
  3. filtrationthe resulting mixture was filtered
  4. customThe filtrate was separated
  5. concentrationconcentrated
  6. extractionextracted with EtOAc (2×100 mL)
  7. washwashed with water (100 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified by column chromatography (silica gel 100-200μ)

Sources & evidence

ORD record
ord-c36ed6207dc34d6bae6ea93ab40cb75f
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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