Bromotrimethylsilane → HCID 178445715, compound

HRID 2404112Notes

Reaction equation

HRID 2404112 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][NH:11][CH2:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH:25]3[CH2:30][CH2:29][CH:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:26]3)=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)=[O:14])(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>C(#N)C>[C:31]([C@H:28]1[CH2:29][CH2:30][C@H:25]([O:24][C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:15]([C:13](=[O:14])[CH2:12][NH:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])[CH2:16][CH2:17]3)[CH2:26][CH2:27]1)([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86668416HCID 86668416, compound

Product 1

HCID 178445715HCID 178445715, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To stirring solution of (2-{2-[5-(4-tert-butyl-cyclohexyloxy)-2,3-dihydro-indol-1-yl]-2-oxo-ethylamino}-ethyl)-phosphonic acid diethyl ester (16 mg, 0.03 mmol) in acetonitrile (0.5 mL) was added bromotrimethylsilane (0.5 mL, 4 mmol). The reaction mixture was stirred at 50° C. overnight. After the solvent was concentrated, the residue was purified by HPLC (acetonitrile-water) to give white precipitate product (7.5 mg, yield: 53%). ESI-MS: 439.2 (M+H)+

Workup

  1. concentrationAfter the solvent was concentrated
  2. customthe residue was purified by HPLC (acetonitrile-water)

Sources & evidence

ORD record
ord-74d4f2b67483436997af76a7ae4ea39b
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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