Sodium hexamethyidisilazane → HCID 59517955, compound

HRID 1025359Notes

Reaction equation

HRID 1025359 reaction equation
[CH3:1][Si](C)(C)N[Si](C)(C)C.[Na].[CH:11]([C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=2[F:34])=[CH:21][CH:20]=1)=O>C1COCC1>[CH:11]([C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=2[F:34])=[CH:21][CH:20]=1)=[CH2:1]

Participants

4

Reactant 2

HCID 45051731Sodium hexamethyidisilazaneHCID 59517949HCID 59517949, compound

Product 1

HCID 59517955HCID 59517955, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of Ph3PCH3Br (75 mg, 0.21 mmol) in THF (4 mL) was added sodium hexamethyldisilazane (NaHMDS) (1 N, 0.21 mL, 0.21 mmol) at −78° C. After stirring at this temperature for 30 min, Compound 100 (70 mg, 0.21 mmol) was added. The reaction solution was allowed to warm up to room temperature and stirred overnight. The solution was quenched with NH4Cl (20 mL) and extracted with EtOAc (30 mL). The organic portion was collected, dried and concentrated. Column chromatography afforded Compound 101 (42 mg, 60%). 1H NMR (300 MHz, CDCl3) δ 7.63-7.51 (m, 3H), 7.45-7.38 (m, 1H), 7.26-7.15 (m, 2H), 7.04-6.97 (m, 2H), 6.45 (dd, J=17.4 and 11.1 Hz, 1H), 5.14 (d, J=17.4 Hz, 1H), 4.86 (d, J=11.4 Hz, 1H), 2.37-2.29 (m, 4H), 1.79-1.72 (m, 4H); ESMS cacld (C21H13F2NO): 339.1; found: 340.1 (M+H).

Workup

  1. stirringstirred overnight
  2. customThe solution was quenched with NH4Cl (20 mL)
  3. extractionextracted with EtOAc (30 mL)
  4. customThe organic portion was collected
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d5ccf91bc85a4257b00052d111b05cb0
Source dataset
uspto-grants-2014_05
Patent number
US08729069B2

Reaction notes

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