Triacetoxyperiodinane → HCID 58010041, compound

HRID 1854482Notes

Reaction equation

HRID 1854482 reaction equation
[Cl:1][C:2]1[C:3]([CH:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[OH:12])=[C:4]2[CH:10]=[CH:9][NH:8][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:11]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[O:12])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 580100785-Chloro-α-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4-methanol

Product 1

HCID 58010041HCID 58010041, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclohexyl)methanol (1.97 g, 7.44 mmol) in DCM (39.4 mL) at about 0° C. was added Dess-Martin periodinane (9.47 g, 22.3 mmol). The reaction mixture was stirred at ambient temperature for about 4 h then quenched by the addition of saturated aqueous Na2SO3 (125 mL). To control the resulting exothermic reaction, the reaction flask was cooled down in an ice bath during the addition. The product was extracted into DCM (3×40 mL) and the combined organic extracts were washed with aqueous NaOH (2 N, 100 mL). The organic phase was dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to provide (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclohexyl)methanone as an off-white solid (1.75 g, 90%); LC/MS (Table 2, Method a) Rt=2.61 min; MS m/z: 263 and 265 (M+H)+. The material was used directly in the next step without further purification.

Workup

  1. customthen quenched by the addition of saturated aqueous Na2SO3 (125 mL)
  2. customthe resulting exothermic reaction
  3. temperaturethe reaction flask was cooled down in an ice bath during the addition
  4. extractionThe product was extracted into DCM (3×40 mL)
  5. washthe combined organic extracts were washed with aqueous NaOH (2 N, 100 mL)
  6. dry with materialThe organic phase was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1ddc135e13d347998d4c1142572be160
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

Loading…