Bromotrimethylsilane → {3,5-Dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxymethyl}-phosphonic acid

HRID 1515024Notes

Reaction equation

HRID 1515024 reaction equation
C([O:3][P:4]([CH2:9][O:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([C:18]2[NH:22][C:21]3[CH:23]=[C:24]([C:27](=[O:39])[NH:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[CH:25]=[CH:26][C:20]=3[N:19]=2)=[C:13]([Cl:40])[CH:12]=1)(=[O:8])[O:5]CC)C.C[Si](Br)(C)C>C(Cl)Cl>[Cl:17][C:15]1[CH:16]=[C:11]([CH:12]=[C:13]([Cl:40])[C:14]=1[C:18]1[NH:22][C:21]2[CH:23]=[C:24]([C:27](=[O:39])[NH:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)[CH:25]=[CH:26][C:20]=2[N:19]=1)[O:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86651276{3,5-Dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxymethyl}-phosphonic acid diethylester

Product 1

HCID 66965913{3,5-Dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxymethyl}-phosphonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {3,5-dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxymethyl}-phosphonic acid diethylester (50 mg, 0.083 mmol) in CH2Cl2 (5 mL) was added TMSBr (0.11 ml, 0.83 mmol) and the solution was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was purified by HPLC to give the title compound as a white solid. 1H NMR (Methanol-d4, 400 MHz): δ 8.84 (d, 1H), 8.56 (d, 1H), 8.21 (d, 2H), 8.15 (d, 1H), 8.03 (m, 2H), 7.90 (d, 1H), 7.80 (t, 1H), 7.37 (s, 2H), 4.49 (d, 2H). MS (m/z) 543.3 (M+1); Retention time: 1.10 min. (method 10).

Workup

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

Sources & evidence

ORD record
ord-b0ab8f9dbc244aaa91515ac34d44c92d
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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