Triacetoxyperiodinane → (5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)((3R)-3-(dibenzylamino)cyclopentyl)methanone

HRID 1854474Notes

Reaction equation

HRID 1854474 reaction equation
[Cl:1][C:2]1[C:3]([CH:21]([CH:23]2[CH2:27][CH2:26][C@@H:25]([N:28]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:24]2)[OH:22])=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:21]([CH:23]2[CH2:27][CH2:26][C@@H:25]([N:28]([CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:24]2)=[O:22])=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([CH:18]([CH3:19])[CH3:20])([CH:15]([CH3:16])[CH3:17])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58009958(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)((3R)-3-(dibenzylamino)cyclopentyl)methanol

Product 1

HCID 58010082(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)((3R)-3-(dibenzylamino)cyclopentyl)methanoneYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of (5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)((3R)-3-(dibenzylamino)cyclopentyl)methanol (1.14 g, 1.89 mmol) in DCM (50 mL) was cooled to about 0° C. Dess-Martin periodinane (2.41 g, 5.68 mmol) was added and the reaction mixture was stirred at about 0-10° C. for about 3 h. The mixture was quenched by a drop-wise addition of aqueous sodium sulfite (1 M, 20 mL), and the organic solvent was removed under reduced pressure. The aqueous layer was extracted with EtOAc (2×25 mL), and the combined organic extracts were washed with aqueous NaOH (1 N, 3×20 mL), brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-20% EtOAc in heptane to yield (5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)((3R)-3-(dibenzylamino)cyclopentyl)methanone (0.68 g, 60%) as a yellow amorphous solid: LC MS (Table 2, Method a) Rt=1.65 min; MS m/z: 442 (M+H)+.

Workup

  1. customThe mixture was quenched by a drop-wise addition of aqueous sodium sulfite (1 M, 20 mL)
  2. customthe organic solvent was removed under reduced pressure
  3. extractionThe aqueous layer was extracted with EtOAc (2×25 mL)
  4. washthe combined organic extracts were washed with aqueous NaOH (1 N, 3×20 mL), brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a gradient of 0-20% EtOAc in heptane

Sources & evidence

ORD record
ord-76c45435b8a544aeaf68f7bf8b2c3c94
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

Loading…