Pyridinium chloride → HCID 178515387, compound

HRID 389528Notes

Reaction equation

HRID 389528 reaction equation
C([O:3][C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][S:10][C:7]2=[CH:8][N:9]=1)C.Cl.N1C=CC=CC=1>O>[S:10]1[C:7]2=[CH:8][N:9]=[C:4]([OH:3])[CH:5]=[C:6]2[CH:12]=[CH:11]1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 66759677HCID 66759677, compound

Product 1

HCID 178515387HCID 178515387, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 5-ethoxythieno[2,3-c]pyridine (127 mg, 0.700 mmol), pyridine hydrochloride (827 mg, 7.00 mmol) and H2O (1.2 mL) was heated in a microwave reactor at 175° C. for 2 h. The reaction mixture was concentrated in vacuo and purified by ISCO chromatography (0 to 15% MeOH:DCM) to afford 58.7 mg (55%) of the title compound as a brown solid. 1H NMR (400 MHz, CDCl3): δ 14.04 (br s, 1 H), 8.12 (s, 1 H), 7.66 (d, J=5.6 Hz, 1 H), 7.07 (dd, J=5.6, 0.4 Hz, 1 H), 6.95 (d, J=0.8 Hz, 1 H); MS (ESI): 152.02 [M+H]+; HPLC tR=0.74 min (TOF: polar—3 min).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by ISCO chromatography (0 to 15% MeOH:DCM)

Sources & evidence

ORD record
ord-08454b68254c42ffb49c3d951dc678fd
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…