Bromotrimethylsilane → 3-(4-((4-(Bis(4-methoxyphenyl)amino)phenyl)(4-methoxyphenyl)amino)phenoxy)propylphosphonic acid

HRID 85000Notes

Reaction equation

HRID 85000 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:28]2[CH:33]=[CH:32][C:31]([N:34]([C:43]3[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=3)[C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)=[CH:30][CH:29]=2)[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>ClCCl>[CH3:50][O:49][C:46]1[CH:47]=[CH:48][C:43]([N:34]([C:35]2[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=2)[C:31]2[CH:30]=[CH:29][C:28]([N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:16]3[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])=[CH:14][CH:15]=3)=[CH:33][CH:32]=2)=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86653414HCID 86653414, compound

Product 1

HCID 667303133-(4-((4-(Bis(4-methoxyphenyl)amino)phenyl)(4-methoxyphenyl)amino)phenoxy)propylphosphonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11. To a dry 25 mL round bottom flask under nitrogen was added diethyl3-(4-((4-(bis(4-methoxyphenyl)amino)phenyl)(4-methoxyphenyl)amino)phenoxy)propylphosphonate (0.500 g, 0.718 mmol) and the flask was purged with nitrogen. Dichloromethane (1.00 mL) and bromotrimethylsilane (0.199 g, 2.30 mmol) were added under nitrogen and the mixture was allowed to stir at room temperature overnight. Upon disappearance of the starting material the solvent was removed through nitrogen purge. Residual solvent was removed in vacuo. Anhydrous methanol (8.00 mL) was added to the flask and allowed to stir at room temperature overnight. White solid was filtered from methanol through cannula filtration. Solid was washed using 3×5 mL anhydrous methanol and dried in vacuo. The product was collected under nitrogen atmosphere as a green solid (0.185 g, 40.2%). 1H NMR (400 MHz, (CD3)2SO) δ 9.87 (s, 2H), 6.89 (m, 8H), 6.83 (m, 8H), 6.71 (s, 4H), 3.91 (m, 2H), 3.69 (s, 9H), 1.84 (m, 2H), 1.51 (m, 2H). 13C {1H} NMR (400 MHz, (CD3)2S, δ): 154.98, 154.40, 142.17, 140.91, 140.77, 125.27, 125.19, 122.72, 122.68, 115.37, 114.82, 68.35 (m), 55.24, 23.62 (m). 31P NMR (400 MHz, (CD3)2S, δ): 25.05. HRMS-EI (m/z): [M]+ calcd for C36H37N2O7P, 640.23; found, 640.1). Anal. Calcd for C36H37N2O7P: C, 67.49; H, 5.82; N, 4.37. Found: C, 67.09; H, 6.16; N, 3.99.

Workup

  1. customthe flask was purged with nitrogen
  2. customUpon disappearance of the starting material the solvent was removed through nitrogen
  3. custompurge
  4. customResidual solvent was removed in vacuo
  5. additionAnhydrous methanol (8.00 mL) was added to the flask
  6. stirringto stir at room temperature overnight
  7. filtrationWhite solid was filtered from methanol through cannula filtration
  8. washSolid was washed
  9. customdried in vacuo
  10. customThe product was collected under nitrogen atmosphere as a green solid (0.185 g, 40.2%)

Sources & evidence

ORD record
ord-eb6d16a8e3994fea9e140ccffe402345
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

Loading…