Triacetoxyperiodinane → HCID 71209353, compound

HRID 1912602Notes

Reaction equation

HRID 1912602 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[C:10]2=[N:11][C:12]([CH3:22])=[C:13]([CH:16]([OH:21])[C:17]([O:19][CH3:20])=[O:18])[C:14]([I:15])=[C:9]2[CH:8]=[CH:7]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[C:10]2=[N:11][C:12]([CH3:22])=[C:13]([C:16](=[O:21])[C:17]([O:19][CH3:20])=[O:18])[C:14]([I:15])=[C:9]2[CH:8]=[CH:7]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 71209104HCID 71209104, compound

Product 1

HCID 71209353HCID 71209353, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate (3.68 g, 6.23 mmol) in DCM (60 mL) at 0° C. was added Dess-Martin periodinane (3.17 g, 7.48 mmol) and the mixture was stirred at RT for 30 min. The mixture was diluted with DCM and washed with saturated Na2S2O3/water, saturated NaHCO3/water (2×), dried (Na2SO4), concentrated, and purified by column chromatography to provide methyl 2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate (3.0 g, 6.06 mmol, 97% yield) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.63 (s, 3 H), 3.98 (s, 3 H), 5.45 (s, 2 H), 6.44 (d, J=3.71 Hz, 1 H), 6.92-7.19 (m, 3 H), 7.23 (d, J=3.71 Hz, 1 H); LCMS (m/z) ES+=471 (M+1).

Workup

  1. washwashed with saturated Na2S2O3/water, saturated NaHCO3/water (2×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-b9b2f6bb339c48078037a2781fb3ed5a
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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