Lithium Hexamethyldisilazide → HCID 21100634, compound

HRID 1724825Notes

Reaction equation

HRID 1724825 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][C:23]=3[O:24][CH3:25])[NH:20][CH:19]=[C:18]4[C:26](=[O:32])[C:27]([N:29]([CH3:31])[CH3:30])=[O:28])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C[Si]([N-:39][Si](C)(C)C)(C)C.[Li+]>CN1CCCC1=O>[NH2:39][N:20]1[C:21]2[C:17](=[CH:16][C:15]([C:13]([N:10]3[CH2:11][CH2:12][CH:7]([CH2:6][C:5]4[CH:33]=[CH:34][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:8][CH2:9]3)=[O:14])=[C:23]([O:24][CH3:25])[CH:22]=2)[C:18]([C:26](=[O:32])[C:27]([N:29]([CH3:30])[CH3:31])=[O:28])=[CH:19]1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 10310740HCID 10310740, compound

Product 1

HCID 21100634HCID 21100634, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2-{5-[4-(4-Fluoro-benzyl)-piperidine-1-carbonyl]-6-methoxy-1H-indol-3-yl}-N,N-dimethyl-2-oxo-acetamide (620 mg, 1.33 mmol) in 1-methyl-2-pyrrolidinone (20 mL) was added lithium bis(trimethylsilyl)amide (2.1 mL, 2.1 mmol, 1.0 M in THF) at −10° C., followed by o-(diphenylphosphinyl)hydroxylamine (350 mg, 1.5 mmol). The reaction mixture was allowed to warm to RT and continually stirred for 6 h, then quenched with water (50 mL). The resulting mixture was extracted with EtOAc, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by radial chromatography eluting with 2% MeOH in CH2Cl2 to give 300 mg (47%) of the desired product as a white solid. M+H+(481).

Workup

  1. customquenched with water (50 mL)
  2. extractionThe resulting mixture was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by radial chromatography
  7. washeluting with 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-b7f466b5e6484c8698fe7a673a3366b3
Source dataset
uspto-grants-2009_02
Patent number
US07488744B2

Reaction notes

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