Cesium carbonate → HCID 59843040, compound

HRID 1878726Notes

Reaction equation

HRID 1878726 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:11])[N:6]([CH2:8][CH2:9]Br)[CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][CH:18]=[C:17]2[OH:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:11])[N:6]([CH2:8][CH2:9][N:20]2[C:21]3[C:16](=[CH:15][C:14]([O:13][CH3:12])=[C:23]([O:24][CH3:25])[CH:22]=3)[C:17](=[O:26])[CH:18]=[CH:19]2)[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 246892801016530-65-6HCID 178486804HCID 178486804, compound

Product 1

HCID 59843040HCID 59843040, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

A suspension of 5-bromo-1-(2-bromoethyl)pyridin-2(1 H)-one (100 mg, 356 μmol), 6,7-dimethoxyquinolin-4-ol (88 mg, 427 μmol), and cesium carbonate (290 mg, 890 μmol) in DMF (2 mL) was stirred at 23° C. for 18 h. The reaction mixture was partitioned between CH2Cl2 and 5% NaHCO3. The aqueous was extracted with CH2Cl2 (2×10 mL) and the combined organics were dried over MgSO4. The solvents were concentrated to an oil from toluene and purified on silica (12 g) eluting with 0-100% of 6% (2M NH3 in MeOH/CH2Cl2). MS (ESI pos. ion) m/z (MH+): 405/407. Calc'd exact mass for C18H17BrN2O4: 404. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.84 (s, 3 H) 4.00 (s, 3 H) 4.25 (t, J=7.04 Hz, 2 H) 4.47 (t, J=7.04 Hz, 2 H) 5.97 (d, J=7.63 Hz, 1 H) 6.44 (d, J=9.59 Hz, 1 H) 7.41 (s, 1 H) 7.50-7.60 (m, 2 H) 7.74 (d, J=7.63 Hz, 1 H) 7.87 (d, J=2.54 Hz, 1H). 13C NMR (101 MHz, DMSO-d6) δ ppm 47.43, 49.21, 55.39, 56.01, 96.58, 98.22, 105.09, 108.26, 120.40, 120.95, 135.41, 139.10, 142.58, 142.96, 146.31, 153.03, 160.30, 175.10.

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 and 5% NaHCO3
  2. extractionThe aqueous was extracted with CH2Cl2 (2×10 mL)
  3. dry with materialthe combined organics were dried over MgSO4
  4. concentrationThe solvents were concentrated to an oil from toluene
  5. custompurified on silica (12 g)
  6. washeluting with 0-100% of 6% (2M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c9b2c15416454e44ac4fc3e3f16f2c44
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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