Methanol → HCID 59402373, compound

HRID 2090306Notes

Reaction equation

HRID 2090306 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO>[Pd]>[Si:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH2:15][NH:16]2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 12129258HCID 12129258, compound

Product 1

HCID 59402373HCID 59402373, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

7-{[tert-Butyl(dimethyl)silyl]oxy}quinoline (0.40 g, 1.5 mmol) in methanol (10 mL, 200 mmol) with 40 mg of 10% Pd on carbon was loaded in a bottle of a Parr Shaker hydrogenator, and shaken for 1 hour under hydrogen atmosphere (50 psi). LC/MS showed that only less than 20% of the reduced product was formed. The reaction mixture continued to be shaken under the same condition for an additional 4 hours. Then LC/MS showed that starting materials were consumed. After filtration, the filtrate was concentrated to yield the desired product. LCMS (M+H)+: m/z=264.3.

Workup

  1. customwas formed
  2. stirringto be shaken under the same condition for an additional 4 hours
  3. customwere consumed
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-004e3a33d70b4e5397ae87b16bb535fe
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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