Sodium Carbonate → Tert-butyl 4-phenylpyridin-2-ylcarbamate

HRID 1245470Notes

Reaction equation

HRID 1245470 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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:16]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11484026(4-Iodo-Pyridin-2-Yl)-Carbamic Acid Tert-Butyl Ester

Product 1

HCID 21912853Tert-butyl 4-phenylpyridin-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (340 mg, 0.29 mmol, 0.050 equiv) was added to a deoxygenated mixture of tert-butyl 4-iodopyridin-2-ylcarbamate (1-1, 1.87 g, 5.84 mmol, 1 equiv), phenyl boronic acid (1.07 g, 8.76 mmol, 1.50 equiv), and aqueous saturated sodium carbonate solution (2.0 M, 8.8 mL, 18 mmol, 3.0 equiv) in dioxane (50 mL), and the resulting mixture was heated at reflux for 18 h. The reaction mixture was cooled then concentrated. The residue was partitioned between half-saturated aqueous NaCl solution (100 mL) and EtOAc (100 mL). The organic layer was dried over sodium sulfate, and concentrated. The residue was purified by flash column chromatography (dichloromethane, initially, grading to 40% EtOAc in dichloromethane) to give tert-butyl 4-phenylpyridin-2-ylcarbamate (1-2) as an off-white solid. LRMS m/z (M+H) Calcd: 214.3 (minus t-Bu), 171.3 (minus Boc); found 215.0 and 171.0.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationthen concentrated
  5. customThe residue was partitioned between half-saturated aqueous NaCl solution (100 mL) and EtOAc (100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (dichloromethane

Sources & evidence

ORD record
ord-11134824e475461eb96b5610241e6401
Source dataset
uspto-grants-2006_10
Patent number
US07125888B2

Reaction notes

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