Triethylamine → tert-butyl 4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylate

HRID 2301119Notes

Reaction equation

HRID 2301119 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.[C:10](=O)([OH:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>ClCCl>[C:12]([O:11][C:10]([N:6]1[CH2:7][CH2:8][C:9]2[S:1][CH:2]=[CH:3][C:4]=2[CH2:5]1)=[O:16])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3015642Mono-tert-butyl carbonateHCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridine

Product 1

HCID 18377286tert-butyl 4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4,5,6,7-Tetrahydro-thieno[3,2-c]pyridine (1.3 g, 9.0 mmol) was dissolved in dichloromethane (25 ml), and the solution was mixed with t-butyl bicarbonate (3.1 ml, 13 mmol) and triethylamine (1.3 ml, 9. 0 mmol) and stirred at room temperature for 13 hours. The reaction solution was mixed with dichloromethane, washed with water and saturated brined and dried with anhydrous sodium sulfate. When the solvent was removed by evaporation from the organic layer under a reduced pressure and the thus obtained material was separated and purified by a silica gel column chromatography, it was able to isolate a part of the title compound, but the most part was obtained as its mixture with t-butyl bicarbonate (total yield, 2.3 g).

Workup

  1. washwashed with water
  2. dry with materialdried with anhydrous sodium sulfate
  3. customWhen the solvent was removed by evaporation from the organic layer under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography, it

Sources & evidence

ORD record
ord-6f5f461b37824990be8bbacdf80258d9
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

Loading…