Sodium ethoxide → HCID 66759677, compound

HRID 389527Notes

Reaction equation

HRID 389527 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][S:8][C:5]2=[CH:6][N:7]=1.[O-:11][CH2:12][CH3:13].[Na+]>CCO>[CH2:12]([O:11][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][S:8][C:5]2=[CH:6][N:7]=1)[CH3:13]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 72207298HCID 72207298, compound

Product 1

HCID 66759677HCID 66759677, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
175 °C

Procedure

A sealable vial was charged with 5-chlorothieno[2,3-c]pyridine (240 mg, 1.41 mmol), sodium ethoxide (557 mg, 7.78 mmol) and EtOH (6.5 mL). The reaction was heated in a microwave reactor at 175° C. for 2 h, then purified by ISCO chromatography (0 to 25% EtOAc:hexane) to afford 174 mg (69%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.69-8.70 (m, 1 H), 7.63 (d, J=5.6 Hz, 1 H), 7.20 (dd, J=5.6, 0.8 Hz, 1 H), 7.08 (d, J=0.8 Hz, 1 H), 4.39 (quartet, J=7.2 Hz, 2 H), 1.43 (t, J=7.2 Hz, 3 H); MS (ESI): 180.04 [M+H]+; HPLC tR=1.39 min (TOF: polar—3 min).

Workup

  1. custompurified by ISCO chromatography (0 to 25% EtOAc:hexane)

Sources & evidence

ORD record
ord-48c2ccdb815f4aa484040d4b8624c6a4
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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