Sodium Bicarbonate → HCID 59830876, compound

HRID 888019Notes

Reaction equation

HRID 888019 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=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.C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([C:28]2[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 68407394HCID 68407394, compound

Product 1

HCID 59830876HCID 59830876, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-(2-t-Butoxycarbonylaminophenyl)-4-bromobenzamide (Method 14; 136 mg, 0.33 mmol), pyridine-4-boronic acid (48 mg, 0.39 mmol), tetrakis(triphenylphosphine) palladium (5 mg, 0.005 mmol), THF (2 ml) and a saturated aqueous solution of sodium hydrogen carbonate (2 ml) were stirred at 55° C. under an atmosphere of argon for 96 hours. The cooled mixture was partitioned between ethyl acetate and water. The organics were washed with brine, dried over magnesium sulfate, filtered and evaporated, to give the title compound (103 mg, 80%), which was used without further purification; Mass Spectrum: M+H+ 390.

Workup

  1. customThe cooled mixture was partitioned between ethyl acetate and water
  2. washThe organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a13b912e22b94a8d98908719811b60df
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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