Water → HCID 57763155, compound

HRID 230749Notes

Reaction equation

HRID 230749 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:3]=1.[N-:15]=[N+]=[N-].[Na+].O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CS(C)=O.C1COCC1.O.CCOC(C)=O>[NH2:15][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 11806045tert-Butyl 4-chloropicolinate

Product 1

HCID 57763155HCID 57763155, compoundYield 52.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
130 °C

Procedure

A mixture of tert-butyl 4-chloropicolinate (3.8 g, 17.8 mmol) and sodium azide (1.74 g, 26.8 mmol) in DMSO (20 mL) was heated at 130° C. for 15 h. The mixture was poured into water (80 mL), extracted three times with EtOAc. The combined organic solutions was dried over MgSO4. The solid was filtered off, and the filtrate was concentrated in vacuo to give a residue which was heated with PPh3 in THF/H2O (9:1,40 mL) at 70° C. overnight. The mixture was diluted with EtOAc, washed with sat. K2HPO4 aq. solution. The organic layer was dried over MgSO4 and the product was purified by flash column chromatography (SiO2, 5% MeOH in EtOAc) to afford a white solid (1.8 g, 52%). LC-MS: m/z 195 (M+H)+.

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined organic solutions was dried over MgSO4
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto give a residue which
  6. washwashed with sat. K2HPO4 aq. solution
  7. dry with materialThe organic layer was dried over MgSO4
  8. customthe product was purified by flash column chromatography (SiO2, 5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-d95078a51d9546c9bd393074cf79a0a3
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

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