Water → HCID 68491840, compound

HRID 1944213Notes

Reaction equation

HRID 1944213 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:15])([CH3:14])[NH:9][CH:10]2[CH3:13])=[CH:5][C:4]=1[OH:16].[K].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:18]([O:16][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[C:10]([CH3:13])=[N:9][C:8]([CH3:15])([CH3:14])[CH2:7]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 5462222PotassiumHCID 68490283HCID 68490283, compound

Product 1

HCID 68491840HCID 68491840, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 239 (970 mg, 4.4 mmol) in acetone (10 ml) was added potassium C(Ar)bonate (3.06 g, 22.0 mmol), benzyl bromide (1.05 ml, 8.8 mmol) and tetrabutyl ammonium iodide (163 mg, 0.44 mmol). The reaction mixture was heated at 55° C. for 60 h. The reaction mixture was cooled to rt, water (20 ml) was added and the aqueous layer was extracted with ethyl acetate (3×30 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography eluting with EtOAc then EtOAc:MeOH:TEA; 10:1:0.1 afforded the title compound (882 mg, 64%) as a pale orange solid. mp=87.9-90° C. 1H NMR (270 MHz; CDCl3) 1.16 (6H, s, 2×CH3), 2.22 (3H, s, CH3), 2.59 (2H, s, CH2), 3.90 (3H, s, OCH3), 5.13 (2H, s, CH2Ph), 6.63 (1H, s, CH), 7.0 (1H, s, CH), 7.27-7.46 (5H, m, 5×CH, phenyl). 13C NMR (67.5 MHz; CDCl3) 23.54 (CH3), 28.15 (2×CH3), 38.70 (CH2), 53.65 (C(CH3)), 56.07 (OCH3), 71.87 (CH2Ph), 111.40 (CH), 112.57 (CH), 121.49 (C), 127.58 (CH), 128.08 (CH), 128.68 (CH), 130.78 (C), 137.15 (C), 146.33 (C), 151.79 (C), 160.65 (C). LC/MS (ES+) tr=2.5 min, m/z 310.05 (M++H). HRMS (ES+) calcd. for C20H24NO2 (M++H) 310.1802, found 310.1801.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×30 ml)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-dc2541e3b13947769e4ddb49ad6c1a62
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

Loading…