Sodium Bicarbonate → HCID 68406977, compound

HRID 888032Notes

Reaction equation

HRID 888032 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:7])=[CH:4][C:3]=1[F:25].[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C(=O)([O-])O.[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[C:18]([O:17][C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6](=[O:7])[C:5]1[CH:23]=[CH:24][C:2]([C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)=[C:3]([F:25])[CH:4]=1)=[O:22])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 68407867HCID 68407867, compound

Product 1

HCID 68406977HCID 68406977, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

t-Butyl 2-[(4-bromo-3-fluorobenzoyl)amino]phenylcarbamate (Method 63, 205 mg, 0.5 mmol), 3-pyridine boronic acid (74 mg, 0.6 mmol), tetrakis(triphenylphosphine) palladium (104 mg, 0.09 mmol), 1,2-dimethoxyethane (3 ml) and a saturated aqueous solution of sodium hydrogen carbonate (3 ml) were stirred at 80° C. under an atmosphere of argon for 48 hours. The cooled mixture was partitioned between ethyl acetate and water. The aqueous layer was removed using Varian Chem Elut column (CE1010) and the resulting solution was then concentrated under reduced pressure and purified by flash column chromatography, eluting with ethyl acetate/isohexane (25-75%), to give the title compound (186 mg, 91%). Mass Spectrum: M+H+ 408.

Workup

  1. customThe cooled mixture was partitioned between ethyl acetate and water
  2. customThe aqueous layer was removed
  3. concentrationthe resulting solution was then concentrated under reduced pressure
  4. custompurified by flash column chromatography
  5. washeluting with ethyl acetate/isohexane (25-75%)

Sources & evidence

ORD record
ord-1269470400e242118af50c87bc84a006
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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