Sodium Thiosulfate → 1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-one

HRID 588159Notes

Reaction equation

HRID 588159 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:11])[C:9]#[CH:10])[C:5]2[C:12]([O:34][CH3:35])=[N:13][N:14]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[C:9]#[CH:10])[C:5]2[C:12]([O:34][CH3:35])=[N:13][N:14]([C:15]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 1182719011-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-ol

Product 1

HCID 1182720611-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-oneYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-ol (257 mg, 0.535 mmol) was dissolved in DCM (5 ml) charged with Dess-MartinPeriodinane (341 mg, 0.803 mmol) and allowed to stir for 2 h at rt. The reaction was charged with 5 mL 1N sodium thiosulfate and 5 mL saturated sodium bicarbonate and allowed to stir for 15 minutes. The organic layer was separated and the solvents were concentrated in vacuo. Purification on silica gel, 10-50% EtOAc/hexanes gave 1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-one (60B, 137 mg, 0.287 mmol, 53.5% yield). MS: [M+H]+ m/z 478.

Workup

  1. stirringto stir for 15 minutes
  2. customThe organic layer was separated
  3. concentrationthe solvents were concentrated in vacuo
  4. customPurification on silica gel, 10-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-cdb8b3ce19054246a0c5f148df91657e
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

Loading…