Sodium Bicarbonate → HCID 89462631, compound

HRID 1473271Notes

Reaction equation

HRID 1473271 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:11]3[C:12](=[O:26])[N:13]([CH3:25])[C:14]([CH2:23][OH:24])=[C:15]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)[C:10]=3[C:9]3[CH2:27][O:28][CH2:29][CH2:30][C:8]2=3)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[C:12](=[O:26])[N:13]([CH3:25])[C:14]([CH:23]=[O:24])=[C:15]([C:16]4[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=4)[C:10]=3[C:9]3[CH2:27][O:28][CH2:29][CH2:30][C:8]2=3)=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 89473316HCID 89473316, compound

Product 1

HCID 89462631HCID 89462631, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice cold suspension of 5-(4-fluorobenzyl)-8-(hydroxymethyl)-7-methyl-9-(p-tolyl)-3,4,5,7-tetrahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridin-6(1H)-one (333 mg, 0.770 mmol) and NaHCO3 (323 mg, 3.85 mmol) in Dichloromethane (DCM) (7700 μl) was treated with DMP (653 mg, 1.540 mmol). Upon complete addition of the DMP the cooling bath was removed. After 2 h, the reaction mixture was quenched by the addition of sat. aq. Na2S2O3 and the mixture was stirred for 10 min. EtOAc was added and the layers partitioned. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by ISCO (0-50% EtOAc-hexanes) to afford 5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde (150 mg, 0.348 mmol, 45.3% yield). LCMS (m/z) ES+=431 (M+1).

Workup

  1. additionwas treated with DMP (653 mg, 1.540 mmol)
  2. additionUpon complete addition of the DMP the cooling bath
  3. customwas removed
  4. customthe reaction mixture was quenched by the addition of sat. aq. Na2S2O3
  5. additionEtOAc was added
  6. customthe layers partitioned
  7. washThe organic layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by ISCO (0-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-9a808bdbf4c14fe5a2fe63f73e53e04f
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

Loading…