Sodium Carbonate → HCID 84819770, compound

HRID 1497443Notes

Reaction equation

HRID 1497443 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[OH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.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>[OH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 98775625-Bromopyridine-2-carbaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 84819770HCID 84819770, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromopicolinaldehyde (0.7 g, 3.76 mmol) in toluene (8 mL) and EtOH (6 mL) was added (4-(hydroxymethyl)phenyl)boronic acid (0.68 g, 4.516 mmol), 2M Na2CO3 (5.6 mL, 11.3 mmol) and Pd(PPh3)4 (0.2 mg, 0.188 mmol) under argon. The mixture was degassed and heated to 100° C. and stirred for 2 h. After completion of the reaction by monitoring with TLC (60% EtOAc\hexane), the resulting mixture was filtered with Celite® reagent and the filtrate was separated. The filtrate was 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 a Biotage Isolera® One column purifier (silica gel 100-200μ) using 38% ethyl acetate in hexane to provide a yellow solid (0.6 g, 75% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.01 (s, 1H), 9.14 (d, 1H), 8.306 (dd, 1H), 7.98 (d, 1H), 7.80 (d, 2H), 7.47 (d, 2H), 5.25 (s, 1H), 4.56 (d, 2H); LC-MS: m/z 214.3 [M+H]+.

Workup

  1. customThe mixture was degassed
  2. customAfter completion of the reaction
  3. filtrationthe resulting mixture was filtered with Celite® reagent
  4. customthe filtrate was separated
  5. concentrationThe filtrate was concentrated
  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 a Biotage Isolera® One column purifier (silica gel 100-200μ)

Sources & evidence

ORD record
ord-a6c7166f376a438ab1f6db19c7d3e0f8
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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