Bromotrimethylsilane → HCID 56933053, compound

HRID 629942Notes

Reaction equation

HRID 629942 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:34][O:35][CH2:36][CH3:37])[N:14]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][P:26](=[O:33])([O:30]CC)[O:27]CC)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C[Si](Br)(C)C>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:34][O:35][CH2:36][CH3:37])[N:14]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][P:26](=[O:27])([OH:30])[OH:33])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86667769HCID 86667769, compound

Product 1

HCID 56933053HCID 56933053, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of diethyl (2-(2-(2-(2-(4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy)ethoxy)ethoxy)ethyl)phosphonate (1 equiv.) in CH2Cl2 (0.10 M) at 0° C. was slowly added trimethylsilyl bromide (10 equiv.). After 1 h the ice-bath was removed and the reaction mixture was allowed to stir at 22° C. for 18 h. At this point the volatiles were removed in vacuo and the resulting residue was purified by Reverse Phase-HPLC using a 20-90% 0.5 mM NH4OAc (in MeCN) to 10 mM NH4OAc (in water) gradient to deliver the title compound (26%) as a solid.

Workup

  1. customat 0° C.
  2. customAfter 1 h the ice-bath was removed
  3. customAt this point the volatiles were removed in vacuo
  4. customthe resulting residue was purified by Reverse Phase-HPLC

Sources & evidence

ORD record
ord-8e9b8e39e13744d480a08676430b8d7f
Source dataset
uspto-grants-2016_04
Patent number
US09315530B2

Reaction notes

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