Sodium Thiosulfate → 6-(3-(4-Ethylpiperazin-1-yl)azetidin-1-yl)-5-fluoropyridine-2-carbaldehyde

HRID 707524Notes

Reaction equation

HRID 707524 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH:9]2[CH2:12][N:11]([C:13]3[N:18]=[C:17]([CH2:19][OH:20])[CH:16]=[CH:15][C:14]=3[F:21])[CH2:10]2)[CH2:5][CH2:4]1)[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([CH:9]2[CH2:12][N:11]([C:13]3[N:18]=[C:17]([CH:19]=[O:20])[CH:16]=[CH:15][C:14]=3[F:21])[CH2:10]2)[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 118162492(6-(3-(4-Ethylpiperazin-1-yl)azetidin-1-yl)-5-fluoropyridin-2-yl)methanol

Product 1

HCID 1181624556-(3-(4-Ethylpiperazin-1-yl)azetidin-1-yl)-5-fluoropyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixed solution of the crude product (402 mg) of (6-(3-(4-ethylpiperazin-1-yl)azetidin-1-yl)-5-fluoropyridin-2-yl)methanol described in Production Example 7-1 and dichloromethane (10.0 mL) was added Dess-Martin periodinane (787 mg, 1.86 mmol) at room temperature. The resultant mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the resultant solution was extracted with dichloromethane. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure to give a crude product (362 mg) of the title compound. The product was used in the subsequent reaction without further purification.

Workup

  1. extractionthe resultant solution was extracted with dichloromethane
  2. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltrated
  4. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-3e84755133444c8890539bfaa4c6f992
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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