Water → HCID 68109870, compound

HRID 404572Notes

Reaction equation

HRID 404572 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:9][C:8]=1[CH2:21][N:22]([CH3:24])[CH3:23].[CH3:25][Si:26]([CH3:29])([CH3:28])Cl.O>C1COCC1>[CH3:23][N:22]([CH2:21][C:8]1[CH:9]=[C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:11]=[CH:12][C:7]=1[Si:26]([CH3:29])([CH3:28])[CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 68109170HCID 68109170, compound2×HCID 178418339Butyllithium

Product 1

HCID 68109870HCID 68109870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −78° C., n-butyl lithium (2.5 ml/L, 3 ml) was slowly added dropwise into a solution of tert-butyl 4-bromo-3-((dimethylamino)methyl)phenylcarbamate (compound 28) (2.7 g, 8 mmol) in THF. The reaction mixture was stirred at low-temperature for 30 minutes, followed by adding trimethylchlorosilane (1.1 g, 9.6 mmol). And then the reaction mixture was stirred at low-temperature for 1 hour. After the mixture was warmed to RT and stirred overnight, three times of water was added into the reaction solution. The reaction mixture was extracted by ethyl acetate. The solvent was dried and evaporated to give a crude product, which can be directly used for the next step.

Workup

  1. stirringAnd then the reaction mixture was stirred at low-temperature for 1 hour
  2. stirringstirred overnight
  3. extractionThe reaction mixture was extracted by ethyl acetate
  4. customThe solvent was dried
  5. customevaporated

Sources & evidence

ORD record
ord-e1f1e0cf671249789c10b4405c3debcf
Source dataset
uspto-grants-2014_06
Patent number
US08748610B2

Reaction notes

Loading…