Water → HCID 22144982, compound

HRID 1825051Notes

Reaction equation

HRID 1825051 reaction equation
C(OC(=O)[NH:7][CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1)[CH2:9][OH:10])(C)(C)C.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21](B(O)O)[CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>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.C(OCC)(=O)C>[NH2:7][CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)[CH:12]=1)[CH2:9][OH:10]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27343783-Pyridinylboronic acidHCID 22134913HCID 22134913, compound

Product 1

HCID 22144982HCID 22144982, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [1-(3-bromo-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester (160 mg, 0.51 mmol) in ethyleneglycoldimethylether (10 mL) in a sealed tube were added pyridine-3-boronic acid (82 mg, 0.66 mmol), cesium carbonate (500 mg, 1.53 mmol) and water (2 mL). Argon was bubbled through the solution for 10 min, and Pd(PPh3)4 (30 mg, 0.025 mmol) was added. The reaction mixture was heated at 100° C. for 6 h. The reaction mixture was cooled down to room temperature, and ethyl acetate (20 mL) was added. The reaction mixture was washed with saturated NH4Cl (2×10 mL), and the organic layer was dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated in vacuo, and the crude product was diluted in CH2Cl2 (8 mL) and trifluoroacetic acid (2 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (110 mg, 100% yield) as brown oil.

Workup

  1. customArgon was bubbled through the solution for 10 min
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. washThe reaction mixture was washed with saturated NH4Cl (2×10 mL)
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. additionthe crude product was diluted in CH2Cl2 (8 mL)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by solid phase extraction (SCX cartridge

Sources & evidence

ORD record
ord-08f3d4fc9e6349c99399e80ec9eba340
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

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