Sodium hexamethyidisilazane → HCID 59517955, compound

HRID 1160744Notes

Reaction equation

HRID 1160744 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 hexamethyidisilazane (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, 3 H), 7.45-7.38 (m, 1 H), 7.26-7.15 (m, 2 H), 7.04-6.97 (m, 2 H), 6.45 (dd, J=17.4 and 11.1 Hz, 1 H), 5.14 (d, J=17.4 Hz, 1 H), 4.86 (d, J=11.4 Hz, 1 H), 2.37-2.29 (m, 4 H), 1.79-1.72 (m, 4 H); ESMS cacld (C21H19F2NO): 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-dde18bcdc2ef40f49dfa944cb893cc7b
Source dataset
uspto-grants-2010_10
Patent number
US07816535B2

Reaction notes

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