Tetrahydrofuran → HCID 124025697, compound

HRID 2209294Notes

Reaction equation

HRID 2209294 reaction equation
[CH3:1][C:2]1([CH3:21])[C:10]2[C:5](=[CH:6][C:7]([B:11]3[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]3)=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:20].I[CH:23]1[CH2:26][O:25][CH2:24]1.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CN(C=O)C.CCOC(C)=O.O.[Cl-].[Na+].O>[CH3:1][C:2]1([CH3:21])[C:10]2[C:5](=[CH:6][C:7]([B:11]3[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]3)=[CH:8][CH:9]=2)[N:4]([CH:23]2[CH2:26][O:25][CH2:24]2)[C:3]1=[O:20]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amide2×HCID 133566863-Iodooxetane2×HCID 669534833,3-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

Product 1

HCID 124025697HCID 124025697, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3,3-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (56 mg, 0.20 mmol) and 3-iodooxetane (85 μL, 0.98 mmol) in DMF (1 mL) was added a THF solution of NaHMDS (1.0 M, 0.21 mL, 0.21 mmol). After 1.5 h, the reaction mixture was heated to 70° C. After an additional 1.5 h, the reaction mixture was cooled to r.t. and additional 3-iodooxetane (30 μL, 0.34 mmol) and NaHMDS solution (0.1 mL, 0.1 mmol) were added. The reaction mixture was heated to 70° C. and was stirred an additional 16 h. The reaction mixture was cooled and diluted with EtOAc, water, and brine, and the layers were separated. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to provide 3,3-dimethyl-1-(oxetan-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (7.43). LCMS-ESI+ (m/z): [M+H]+ calcd for C19H27BNO4: 344.20; found: 316.25.

Workup

  1. waitAfter an additional 1.5 h
  2. temperaturethe reaction mixture was cooled to r.t.
  3. temperatureThe reaction mixture was heated to 70° C.
  4. temperatureThe reaction mixture was cooled
  5. customthe layers were separated
  6. washThe organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a2bdf0fca5c94108bb56870e1feb231d
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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