Potassium Carbonate → 6-[(3-Chloro-pyridin-4-ylmethyl)-amino]-pyridine-3-carbaldehyde

HRID 1754742Notes

Reaction equation

HRID 1754742 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][C:10]1[N:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][C:10]1[N:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 576192366-[(3-Chloro-pyridin-4-ylmethyl)-amino]pyridin-3-yl-methanol

Product 1

HCID 576192126-[(3-Chloro-pyridin-4-ylmethyl)-amino]-pyridine-3-carbaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-[(3-chloro-pyridin-4-ylmethyl)-amino]-pyridin-3-yl-methanol (556, 0.50 g, 2.00 mmol) in tetrahydrofuran (20.0 mL) was added Dess-Martin periodinane (1.02 g, 2.40 mmol). The reaction was stirred at room temperature for 10 minutes, then poured into aqueous potassium carbonate, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give crude compound (557, 0.45 g, 91%) that was used in the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-26dd6933a6f942c29d4f311eb5e26ece
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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