Sodium Iodide → 4-(2-Oxazolo[4,5-c]pyridin-2-ylvinyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 217186Notes

Reaction equation

HRID 217186 reaction equation
[Na+].[I-].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH:17](Cl)[C:18]2[O:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][C:21]=3[N:26]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>N1C=CC=CC=1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH:16]=[CH:17][C:18]2[O:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][C:21]=3[N:26]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 576595584-(2-Chloro-2-oxazolo[4,5-c]pyridin-2-ylethyl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 689463884-(2-Oxazolo[4,5-c]pyridin-2-ylvinyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

NaI (2 mg) was added to a solution of 4-(2-chloro-2-oxazolo[4,5-c]pyridin-2-ylethyl)-piperidine-1-carboxylic acid tert-butyl ester (Example 22, 18 mg, 49 μmol) in anhydrous pyridine (1 mL). The mixture was heated under microwave irradiation for 10 min at 150° C., before being concentrated in vacuo. The residue was taken up in EtOAc (20 mL), then the EtOAc solution was washed with a mixture of saturated aqueous NaHCO3 and saturated aqueous Na2S2O3 (1:1, 2×8 mL), before being dried (MgSO4). Filtration, solvent evaporation, and flash chromatography (EtOAc-IH, 17:3) yielded 4-(2-oxazolo[4,5-c]pyridin-2-ylvinyl)-piperidine-1-carboxylic acid tert-butyl ester as a 1:1 mixture of (E)- and (Z)-isomers: m/z (ES+)=330.1 [M+H]+. A solution of this compound (10 mg, 30 μmol) in EtOH (1 mL) was stirred with Pd (10% on C, 1 mg) under a H2 atmosphere for 4 h. The mixture was filtered through celite, washing with MeOH. The combined filtrates were concentrated under reduced pressure to afford the title compound: RT=2.89 min; m/z (ES+)=332.2 [M+H]+.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. washthe EtOAc solution was washed with a mixture of saturated aqueous NaHCO3 and saturated aqueous Na2S2O3 (1:1, 2×8 mL)
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationFiltration, solvent evaporation, and flash chromatography (EtOAc-IH, 17:3)

Sources & evidence

ORD record
ord-17bcba8da17e47a2813a5a0636105cf9
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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