Potassium Carbonate → HCID 22391162, compound

HRID 2113100Notes

Reaction equation

HRID 2113100 reaction equation
Br[C:2]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[OH:10][CH2:9][C:7]1[CH:6]=[CH:5][C:3]([NH2:4])=[C:2]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 22391294HCID 22391294, compound

Product 1

HCID 22391162HCID 22391162, compoundYield 138%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

To a degassed solution of crude 2-bromo-4-hydroxymethylaniline (3.2 g, 15.8 mmol), 4-methoxybenzeneboronic acid (2.89 g, 19 mmol) and potassium carbonate (4.77 g, 34.8 mmol) in toluene/ethanol 2/1 (45 mL) a catalytic amount of Pd(PPh3)4 (0.2 g, 1 mmol %) was added and the mixture was heated at 90 C for 5 hours. The residue was extracted into ethyl acetate and washed with water and then saturated brine and dried over sodium sulphate. The solvent was removed under reduced pressure to afford 5 g of crude product. C14H15BNO2 Mass (calculated) [229.28]; (found) [M+H+]=230 Lc Rt=0.88, 89%. NMR (400 MHz, CDCl3): 3.75 (3H, s, MeO); 4.5 (2H, s, CH2O); 6.65 (1H, d, J=8.5 Hz, aryl-H); 6.9 (2H, d, J=8.5 Hz, aryl-H); 7-7.1 (2H, m, aryl-H); 7.25 (2H, d, J=8.5 Hz, aryl-H).

Workup

  1. temperaturethe mixture was heated at 90 C for 5 hours
  2. extractionThe residue was extracted into ethyl acetate
  3. washwashed with water
  4. dry with materialsaturated brine and dried over sodium sulphate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-79fbffd0bf5a4e5e8045f1fe8546cf63
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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