Bromotrimethylsilane → HCID 11625391, compound

HRID 229457Notes

Reaction equation

HRID 229457 reaction equation
[P:1]([O:28]C)([O:26]C)([O:3][C:4]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[N:10]([CH2:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[N:9]=1)=[C:5]([CH3:7])[CH3:6])=[O:2].C[Si](Br)(C)C>C(Cl)Cl.CC#N.O>[P:1]([OH:26])([OH:28])([O:3][C:4]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[N:10]([CH2:19][C:20](=[O:25])[C:21]([CH3:23])([CH3:22])[CH3:24])[N:9]=1)=[C:5]([CH3:7])[CH3:6])=[O:2]

Participants

6

Reactant 2

HCID 76113BromotrimethylsilaneHCID 115319381-[1-(3,3-Dimethyl-2-oxobutyl)-6-methoxy-1H-indazol-3-yl]-2-methylprop-1-en-1-yl dimethyl phosphate

Product 1

HCID 11625391HCID 11625391, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 120 mg 1-[1-(3,3-dimethyl-2-oxobutyl)-6-methoxy-1H-indazol-3-yl]-2-methylprop-1-en-1-yl dimethyl phosphate from Example 1 in 0.75 mL anhydrous DCM. Cool the solution in an ice bath under nitrogen. Add 108 mg trimethylsilyl bromide and let the reaction mixture sit at room temperature for 2.5 hours. Remove solvent under reduced pressure. The residue was dissolved in a mixture of MeCN and water and purified by RP-HPLC using 10-100% MeCN gradient with about 0.05% TFA to give the title compound as a colorless solid after lyophilization. This reaction can also be carried out in MeCN. The title compound can also be purified by recrystallization in anhydrous MeCN.

Workup

  1. temperatureCool the solution in an ice bath under nitrogen
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-70caa72d7452409da9e1f557cc44deca
Source dataset
uspto-grants-2009_07
Patent number
US07563816B2

Reaction notes

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