Sodium hydride → HCID 19877952, compound

HRID 1885835Notes

Reaction equation

HRID 1885835 reaction equation
[H-].[Na+].[F:3][C:4]([F:16])([F:15])[C:5]1[N:6]=[C:7]([C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[NH:8][CH:9]=1.[CH3:17][Si:18]([CH2:21][CH2:22][O:23][CH2:24]Cl)([CH3:20])[CH3:19]>CCCCCC>[F:16][C:4]([F:3])([F:15])[C:5]1[N:6]=[C:7]([C:10]2[N:14]([CH2:24][O:23][CH2:22][CH2:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:13]=[CH:12][N:11]=2)[N:8]([CH2:24][O:23][CH2:22][CH2:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178506252HCID 178506252, compound

Product 1

HCID 19877952HCID 19877952, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 14.4 g (0.3 mol) 50% NaH (washed 3 times with hexane to remove the mineral oil) and 300 ml DMF, was slowly added 26.3 g (0.13 mol) 4-(trifluoromethyl)-2,2'-bi-1H-imidazole as a solid. The reaction was stirred for 2 hours at room temperature and then heated at 40° C. for 2 hours. Next, 50 g (0.3 mol) SEM-Cl was added dropwise. After 1 hour, the reaction was quenched with water (1 liter) and the product extracted into EtOAc (3×150 ml). After drying (NaSO4) and concentration, 51.2 g crude product was obtained. Purification by preparative HPLC (37% EtOAc/63% hexane) gave 16.7 g (28%) desired product as a tan oil; 1H NMR (CDCl3) δ-0.14 (s, 18), 0.61-1.0 (m, 4), 3.25-3.70 (m, 4), 5.76 (s, 2), 5.81 (s, 2), 0.61-1.0 (m, 4), 3.25-3.70 (m, 4), 5.76 (s, 2), 5.81 (s, 2), 6.91-7.06 (m, 2), 7.36 (s br, 1); MS (CI/CH4) m/z 463 (MH+).

Workup

  1. customto remove the mineral oil) and 300 ml DMF
  2. temperatureheated at 40° C. for 2 hours
  3. waitAfter 1 hour
  4. customthe reaction was quenched with water (1 liter)
  5. extractionthe product extracted into EtOAc (3×150 ml)
  6. customAfter drying
  7. concentration(NaSO4) and concentration
  8. custom51.2 g crude product was obtained
  9. customPurification by preparative HPLC (37% EtOAc/63% hexane)

Sources & evidence

ORD record
ord-ff565abe766f48d49158dc6e73e024dd
Source dataset
uspto-grants-1992_09
Patent number
US05147863

Reaction notes

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