Benzaldehyde → HCID 68556789, compound

HRID 1869182Notes

Reaction equation

HRID 1869182 reaction equation
C([Si](C)(C)[N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[CH:8]=[CH:7]1)(C)(C)C.[CH3:17][C:18]1([CH3:26])[O:25][C:23](=[O:24])[CH2:22][C:20](=[O:21])[O:19]1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.N1CCC[C@H]1C(O)=O>C(#N)C>[CH3:17][C:18]1([CH3:26])[O:25][C:23](=[O:24])[CH:22]([CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:6][CH:7]=2)[C:20](=[O:21])[O:19]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 145742L-ProlineHCID 108472111-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68556789HCID 68556789, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a room temperature (RT) solution of 1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine (Synthesis 1999, 615-620) (2.88 g, 9.47 mmol) in acetonitrile (20 ml) was added Meldrum's acid (1.5 g, 10 mmol), benzaldeyde (1.9 ml, 19 mmol) triethylamine (TEA) (1.9 ml, 14 mmol) and proline (catalytic quantity). The mixture was stirred overnight at RT, concentrated, and the residue was partitioned between EtOAc and brine. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc), affording 2,2-dimethyl-5-[phenyl-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-[1,3]dioxane-4,6-dione.

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between EtOAc and brine
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-0e0993b0b4ba4805898bba5fb6ab1758
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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