Triacetoxyperiodinane → HCID 58529936, compound

HRID 1972812Notes

Reaction equation

HRID 1972812 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:14]=3)[CH:9]=[C:10]([CH2:11][OH:12])[N:6]2[N:5]=[CH:4][N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:14]=3)[CH:9]=[C:10]([CH:11]=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58529973HCID 58529973, compound

Product 1

HCID 58529936HCID 58529936, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-amino-5-[3-(benzyloxy)phenyl]pyrrolo[2,1-f][1,2,4]triazin-7-yl}methanol (300 mg, 0.87 mmol) in dichloromethane (5 mL) was added Dess-Martin Periodinane (492 mg, 1.13 mmol). The mixture was stirred (rt) for 4 h. The reaction was quenched with the addition of a 1:1 mixture of saturated, aqueous NaHCO3 and saturated aqueous Na2S2O3 solutions (5 mL) and the mixture was allowed to stir at it for 1 h. The mixture was extracted with dichloromethane (3×5 mL) and the combined organics were washed with brine, dried (Na2SO4) and concentrated to afford 105 mg (35%) of the desired product, which was used without further purification. ES-MS m/z 345.2 [M+H]+, HPLC RT (min) 3.12.

Workup

  1. customThe reaction was quenched with the addition of a 1:1 mixture of saturated, aqueous NaHCO3 and saturated aqueous Na2S2O3 solutions (5 mL)
  2. stirringto stir at it for 1 h
  3. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20f79d88ba6940f482abb33205a4a36b
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…