Sodium bis(trimethylsilyl)amide → 6-Bromo-3,3-dimethyl-1-(2-trimethylsilylethoxymethyl)indolin-2-one

HRID 1507593Notes

Reaction equation

HRID 1507593 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[N:8]2[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 106576496-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 900463446-Bromo-3,3-dimethyl-1-(2-trimethylsilylethoxymethyl)indolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 6-bromo-3,3-dimethylindolin-2-one (example 14a, 4.87 g, 20.3 mmol) in THF (135 ml) was cooled to 0° C. and a solution of sodium bis(trimethylsilyl)amide in THF (1M, 24.3 ml, 24.3 mmol) was added during 15 minutes. Then a solution of (2-(chloromethoxy)ethyl)trimethylsilane (4.27 g, 4.54 ml, 24.3 mmol) in THF (5 ml) was added during 15 minutes. After 4 hours at 0° C. the reaction mixture was poured into ice-water.

Sources & evidence

ORD record
ord-13a59896239746628c8c4dd5981abcae
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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