Water → HCID 67499538, compound

HRID 1502584Notes

Reaction equation

HRID 1502584 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([N:7]([CH2:15][CH3:16])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:6]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(O)C>[CH2:15]([N:7]([N:5]1[CH:6]=[C:2]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[N:3]=[CH:4]1)[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 69640512HCID 69640512, compound

Product 1

HCID 67499538HCID 67499538, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

tert-Butyl (4-bromo-1H-imidazol-1-yl)(ethyl)carbamate (253.7 mg, 0.874 mmol), pyridin-3-ylboronic acid (113 mg, 0.918 mmol), potassium carbonate (329 mg, 2.39 mmol), water (0.870 mL), absolute ethanol (1.74 mL), and toluene (3.50 mL) were placed into a 10 mL round bottomed flask equipped with condenser and magnetic stirrer. The atmosphere was flushed with nitrogen and tetrakis triphenylphosphine palladium (30.0 mg, 0.026 mmol) was added. The mixture was heated to 110° C. and stirred for 16 hours. The reaction was cooled, the organic layer set aside, and the aqueous layer was extracted with ethyl acetate. All organics were combined, dried over sodium sulfate, and concentrated. The residue was purified using silica gel chromatography (0-25% methanol/dichloromethane) to afford the title compound (81 mg, 0.28 mmol, 32%) as a yellow oil: 1H NMR (400 MHz, CD3CN) δ 9.00 (d, J=2.5 Hz, 1H), 8.46 (d, J=4.8 Hz, 1H), 8.11 (m, 1H), 7.67 (d, J=1.3 Hz, 1H), 7.61 (d, J=1.2 Hz, 1H), 7.36 (m, 1H), 3.76 (q, J=7.1 Hz, 2H), 1.45 (s, 9H), 1.17 (t, J=7.2 Hz, 3H); ESIMS m/z 289 ([M+H]+).

Workup

  1. customequipped with condenser and magnetic stirrer
  2. additionwas added
  3. temperatureThe reaction was cooled
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-2b748b41d508450fb0c04ab49620c166
Source dataset
uspto-grants-2015_12
Patent number
US09210931B2

Reaction notes

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