Trimethylsilyl cyanide → HCID 59511834, compound

HRID 1157949Notes

Reaction equation

HRID 1157949 reaction equation
C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].[C:26]([O:30][C:31](=[O:42])[NH:32][CH2:33][C:34]1[CH:39]=[C:38]([NH2:40])[CH:37]=[CH:36][C:35]=1[Br:41])([CH3:29])([CH3:28])[CH3:27].[Si:43]([O:50][C:51]1[C:52]([F:61])=[C:53]([CH:56]=[C:57]([CH2:59][CH3:60])[CH:58]=1)[CH:54]=O)([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44].C[Si]([C:66]#[N:67])(C)C>ClCCl>[C:26]([O:30][C:31](=[O:42])[NH:32][CH2:33][C:34]1[CH:39]=[C:38]([NH:40][CH:54]([C:53]2[CH:56]=[C:57]([CH2:59][CH3:60])[CH:58]=[C:51]([O:50][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C:52]=2[F:61])[C:66]#[N:67])[CH:37]=[CH:36][C:35]=1[Br:41])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 25232416HCID 25232416, compoundHCID 598380723-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

Product 1

HCID 59511834HCID 59511834, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of Yb(OTf)3 (0.399 g) and dichloromethane (20 mL) there were added (5-amino-2-bromobenzyl)carbamic acid t-butyl ester (1.95 g), 3-(t-butyldimethylsilanyloxy)-5-ethyl-2-fluorobenzaldehyde (1.83 g), MS3A (2.6 g) and trimethylsilyl cyanide (1.29 mL) in that order under a nitrogen atmosphere, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off under reduced pressure, ethyl acetate (200 mL) and water (100 mL) were added to the residue, and after sufficiently shaking the mixture, the organic layer was separated off, washed with saturated aqueous sodium chloride (100 mL) and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (3.09 g) as a colorless solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, ethyl acetate (200 mL) and water (100 mL)
  2. additionwere added to the residue
  3. stirringafter sufficiently shaking the mixture
  4. customthe organic layer was separated off
  5. washwashed with saturated aqueous sodium chloride (100 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customto obtain a filtrate
  9. distillationthe solvent in the filtrate was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

Sources & evidence

ORD record
ord-70f4614b7d0348cdacb8d2d7fd5aff7e
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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