Sodium hydride → HCID 59843078, compound

HRID 1878707Notes

Reaction equation

HRID 1878707 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[H-].[Na+].[C:11]([NH:18][CH2:19][CH2:20]Br)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:20][CH2:19][NH:18][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5995285-Bromo-2-hydroxypyridineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 59843078HCID 59843078, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a stirring solution of 5-bromo-2(1h)-pyridone (550 mg, 3161 μmol) in DMF (5 mL) under nitrogen was added NaH (60% dispersion in mineral oil; 152 mg, 6322 μmol). After for 10 min, 2-(boc-amino) ethyl bromide (779 mg, 3477 μmol) was added. The mixture was stirred for 18 h at 23° C. The mixture was partitioned between CH2Cl2 and 5% NaHCO3. The aqueous was extracted with CH2Cl2 (10 mL) twice. The combined organics were dried over MgSO then concentrated to a solid from toluene under reduced pressure. The residue was purified on silica (40 g) eluting with 0-30% of 5% MeOH/CH2Cl2 to give the product as a white solid. MS (ESI pos. ion) m/z (MH+): 317/319. Calc'd exact mass for C12H17BrN2O3: 316. 1H NMR (400 MHz, Chloroform-d) δ ppm 1.44 (s, 9H) 3.45 (q, J=6.02 Hz, 2H) 4.03-4.09 (m, 2H) 4.92 (br. s., 1H) 6.48 (d, J=10.04 Hz, 1H) 7.34-7.39 (m, 2H). 13C NMR (101 MHz, Chloroform-d) δ ppm 26.08, 37.26, 47.20, 95.56, 119.79, 135.87, 140.53

Workup

  1. customThe mixture was partitioned between CH2Cl2 and 5% NaHCO3
  2. extractionThe aqueous was extracted with CH2Cl2 (10 mL) twice
  3. dry with materialThe combined organics were dried over MgSO
  4. concentrationthen concentrated to a solid from toluene under reduced pressure
  5. customThe residue was purified on silica (40 g)
  6. washeluting with 0-30% of 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-2d0ccf521f484c689c11a626009de591
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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