Bromotrimethylsilane → HCID 86659560, compound

HRID 1431015Notes

Reaction equation

HRID 1431015 reaction equation
C([O:4][P:5]([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[C:22]([C:24](=[O:31])[NH:25][C:26]3[S:27][CH:28]=[CH:29][N:30]=3)[CH:21]=[C:20]([S:32][C:33]3[N:34]([CH3:38])[CH:35]=[CH:36][N:37]=3)[CH:19]=2)=[CH:13][CH:12]=1)(=[O:10])[O:6]C(C)C)(C)C.[Br:39][Si](C)(C)C>C(Cl)Cl>[BrH:39].[CH3:38][N:34]1[CH:35]=[CH:36][N:37]=[C:33]1[S:32][C:20]1[CH:19]=[C:18]([CH:23]=[C:22]([C:24](=[O:31])[NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[CH:21]=1)[O:17][C:14]1[CH:15]=[CH:16][C:11]([P:5](=[O:4])([OH:6])[OH:10])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86659561HCID 86659561, compound

Product 1

HCID 86659560HCID 86659560, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to Example 1, a mixture of {4-[3-(1-methyl-1H-imidazol-2-ylsulfanyl)-5-(thiazol-2-ylcarbamoyl)-phenoxy]-phenyl}-phosphonic acid diisopropyl ester (58 mg, 0.10 mmol) and bromotrimethylsilane (0.27 mL, 2.03 mmol) in 2 mL CH2Cl2 was stirred for 16 h at rt. The solvent evaporated, the residue dissolved in CH3CN and then the solvent evaporated, and the residue sonicated in a mixture of 1 mL CH3CN and 0.1 mL water. The resulting white solid was collected by filtration and dried under high vacuum to provide 30 mg (61%) of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 3.84 (s, 3H), 7.14 (dd, 2H, J=8, 3 Hz), 7.30 (d, 1H, J=4 Hz), 7.38 (br s, 1H), 7.55 (d, 1H, J=4 Hz), 7.72 (d, 1H, J=1 Hz), 7.72 (dd, 2H, J=12, 8 Hz), 7.76 (br s, 1H), 7.80 (t, 111, J=2 Hz), 7.88 (d, 1H, 1=1 Hz); LCMS (m/z): 489.5 [C20H17N4O5PS2+H]+. Anal. calcd. for (C20H17N4O5PS2+1.5HBr+1.5H2O): C, 37.72; H, 3.40; N, 8.80. Found: C, 37.94; H, 3.44; N, 8.58.

Workup

  1. customThe solvent evaporated
  2. dissolutionthe residue dissolved in CH3CN
  3. customthe solvent evaporated
  4. customthe residue sonicated in a mixture of 1 mL CH3CN and 0.1 mL water
  5. filtrationThe resulting white solid was collected by filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-639dbe5bd5a24094b6916d9a4a16f156
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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