Bromotrimethylsilane → HCID 25235408, compound

HRID 1360784Notes

Reaction equation

HRID 1360784 reaction equation
C([O:3][P:4]([CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([C:19]2[NH:23][C:22]3[CH:24]=[C:25]([C:28]4[O:29][C:30]([C:33]5[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=5)=[N:31][N:32]=4)[CH:26]=[CH:27][C:21]=3[N:20]=2)=[C:14]([CH3:40])[CH:13]=1)(=[O:8])[O:5]CC)C.C[Si](Br)(C)C>C(Cl)Cl>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C:30]2[O:29][C:28]([C:25]3[CH:26]=[CH:27][C:21]4[N:20]=[C:19]([C:15]5[C:16]([CH3:18])=[CH:17][C:12]([CH2:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])=[CH:13][C:14]=5[CH3:40])[NH:23][C:22]=4[CH:24]=3)=[N:32][N:31]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86632824HCID 86632824, compound

Product 1

HCID 25235408HCID 25235408, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(E)-3-(4-{6-[5-(4-chlorophenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-3,5-dimethylphenyl)-allyl]-phosphonic acid diethyl ester (1.44 g, 2.5 mmol) in CH2Cl2 (15 mL) was added trimethylsilylbromide (1.62 mL, 12.5 mmol) and the mixture was stirred at RT for 18 h. The solvent was removed under reduced pressure and the residue was purified by reverse phase HPLC using a gradient of 0-80% MeCN/water containing 0.7% NH4OH to give the title compound. MS: m/z 523.1 (M+1). H1-NMR (DMSO-d6): δ ppm 8.46 (s, 0.6H), 8.19 (d, J=8.59 Hz, 2H), 8.0 (d, J=8.21 Hz, 1H), 7.88 (s broad, 0.4H), 7.72 (d, J=8.59 Hz, 2H), 7.05 (s, 2H), 2.64 (t, 2H), 2.11 (s, 6H), 1.78 (m, 2H), 1.41 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f2079f6f40c949ab8e8afb3883187892
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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