Ethyl Acetate → HCID 89924318, compound

HRID 1752647Notes

Reaction equation

HRID 1752647 reaction equation
[OH:1][CH:2]([C:7]1[C:8]([I:18])=[C:9]2[CH:16]=[CH:15][N:14]([CH3:17])[C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C(OCC)(=O)C>ClCCl>[I:18][C:8]1[C:7]([C:2](=[O:1])[C:3]([O:5][CH3:6])=[O:4])=[C:12]([CH3:13])[N:11]=[C:10]2[N:14]([CH3:17])[CH:15]=[CH:16][C:9]=12

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 89923660HCID 89923660, compound

Product 1

HCID 89924318HCID 89924318, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An 0° C. solution of methyl 2-hydroxy-2-(4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (12.0 g, 33.3 mmol) in dichloromethane (DCM) (120 mL) was treated with Dess-Martin periodinane (19.84 g, 46.8 mmol) in one portion and warmed to ambient temperature. After 18 h, sat. aq. Na2S2O3 was added and the reaction mixture was stirred for 20 min. Ethyl acetate was added and the layers partitioned. The organic phase was washed with sat. aq. NaHCO3, brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by ISCO (0-30% EtOAc-hexanes) to afford methyl 2-(4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate (9.6 g, 26.8 mmol, 74.5% yield) as light yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.58 (s, 3H) 3.86 (s, 3H) 3.93 (s, 3H) 6.35 (d, J=3.52 Hz, 1H) 7.22 (d, 1H). LC/MS (m/z) ES+=359.9 (M+1)+

Workup

  1. customthe layers partitioned
  2. washThe organic phase was washed with sat. aq. NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by ISCO (0-30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-3ccc2250e8a64a48bb6a41ef1596205d
Source dataset
uspto-grants-2015_10
Patent number
US09163023B2

Reaction notes

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