Diisopropylethylamine → HCID 58608093, compound

HRID 2243587Notes

Reaction equation

HRID 2243587 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([O:14]CC2C=CC=CC=2)=[C:10](I)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH2:33]([Si:35]([C:40]#[C:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH2:38][CH3:39])[CH2:36][CH3:37])[CH3:34]>CN(C=O)C>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[C:10]2[C:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[C:40]([Si:35]([CH2:38][CH3:39])([CH2:33][CH3:34])[CH2:36][CH3:37])[O:23][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11085224HCID 11085224, compoundHCID 22050830HCID 22050830, compound

Product 1

HCID 58608093HCID 58608093, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A 250-ml round bottom flask was charged with 1-benzyl-4-benzyloxy-3-iodo-2-pyridone (6.00 g, 14.40 mmol), dichloro[1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (1.18 g, 1.44 mmol), DMF (60 mL), Hunig's base (3 mL, 17.30 mmol), triethylsilyl phenylacetylene (9.34 g, 43.10 mmol). The system was evacuated and purged with N2 three times, and the reaction was stirred at 110° C. for 12 hrs. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried over Na2SO4 and the solvent was removed. The residue was purified by silica gel column chromatography, eluting with 50/50/1, EtOAc/Hexane/MeOH, to give 7-benzyl-3-phenyl-2-(triethylsily)furo[2,3-b]pyridine-4(7H)-one as a solid. MS (MH+) 416.0; Calculated 415 for C26H29NO2Si.

Workup

  1. customThe system was evacuated
  2. custompurged with N2 three times
  3. additionThe reaction mixture was diluted with EtOAc
  4. washwashed with water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was removed
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 50/50/1, EtOAc/Hexane/MeOH

Sources & evidence

ORD record
ord-9a415e59429341be8a689c9ccbf7eaad
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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