Sodium Carbonate → HCID 86590138, compound

HRID 1840527Notes

Reaction equation

HRID 1840527 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:16])[C:7]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[Br:16][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86590139HCID 86590139, compound

Product 1

HCID 86590138HCID 86590138, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1,1-dimethylethyl (3,5-dibromo-4-pyridyl)carbamate (4.2 g; 12.0 mmol), phenylboronic acid (1.76 g; 14.4 mmol), sodium carbonate (3.1 g; 29.2 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.416 g; 0.36 mmol) in dioxane (24 ml) and water (12 ml) is heated at 70° C. under argon for 8 hours. The reaction mixture is concentrated under reduced pressure. The residue obtained is taken up in ethyl acetate (200 ml), washed with water (2×100 ml) and brine (100 ml), dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue is chromatographed on a column of silica, eluting with an ethyl acetate/cyclohexane gradient of from 0 to 5%. 2.3 g of 1,1-dimethylethyl (3-bromo-5-phenylpyrid-4-yl)carbamate are isolated in the form of a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe residue obtained
  3. washwashed with water (2×100 ml) and brine (100 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is chromatographed on a column of silica
  8. washeluting with an ethyl acetate/cyclohexane gradient of from 0 to 5%

Sources & evidence

ORD record
ord-3cec82aa3f034cc1ba8432d6388d77e9
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

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