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Sodium bis(trimethylsilyl)amide → 6-Bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one

HRID 2209286
Notes
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Reaction equation

HRID 2209286 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([F:13])([F: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]>CN(C=O)C.C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([F:13])([F: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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 722182316-Bromo-3,3-difluoroindolin-2-one

Product 1

HCID 1234084286-Bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

Into the solution of 6-bromo-3,3-difluoroindolin-2-one in DMF (5 mL), was added 1M of NaHMDS solution in THF (1.6 mL), after 30 min., (2-(chloromethoxy)ethyl)trimethylsilane (269 mg) was added. After being stirred at rt for 4 h, the reaction mixture was extracted with ethyl acetate and washed with brine, dried and the solvent was removed, the residue was purified by silica gel chromatography to provide 0.46 g of 6-bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one 7.35. 1H NMR (400 MHz, Chloroform-d) δ 7.43 (s, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.33 (d, J=8.1 Hz, 1H), 5.12 (s, 2H), 3.58 (m, 2H), 1.21 (m, 2H), 0.00 (s, 9H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. customdried
  4. customthe solvent was removed
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1de3a3149b704a3b981a834be4a6fa62
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376441B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes