2-Pyridinemethanamine → (3-Phenyl-thieno[2,3-b]pyridin-4-yl)-pyridin-2-ylmethyl-amine

HRID 2104104Notes

Reaction equation

HRID 2104104 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[S:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:3]=12.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>C(Cl)Cl>[C:11]1([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 684343754-Chloro-3-phenylthieno[2,3-b]pyridine

Product 1

HCID 11709483(3-Phenyl-thieno[2,3-b]pyridin-4-yl)-pyridin-2-ylmethyl-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-3-phenyl-thieno[2,3-b]pyridine (47 mg, 0.19 mmol) and 2-aminomethyl pyridine (0.5 ml, 4.85 mmol) were placed in a 10 ml glass tube. The vessel was sealed with a septum and placed in the microwave cavity. Using microwave irradiation the temperature was ramped from room temperature to 150° C. Once 150° C. was reached, the reaction mixture was held at this temperature for 90 minutes. After cooling to room temperature, the temperature was ramped to 200° C. and held at this temperature for 30 min. After cooling, the reaction mixture was diluted with DCM and washed with water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give (3-phenyl-thieno[2,3-b]pyridin-4-yl)-pyridin-2-ylmethyl-amine. Yield=14 mg, 23%.

Workup

  1. customThe vessel was sealed with a septum
  2. custommicrowave irradiation the temperature
  3. customwas ramped from room temperature to 150° C
  4. customOnce 150° C.
  5. customwas ramped to 200° C.
  6. waitheld at this temperature for 30 min
  7. temperatureAfter cooling
  8. washwashed with water
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b242aa7ffd68400982ce632bcba0e81c
Source dataset
uspto-grants-2009_08
Patent number
US07576212B2

Reaction notes

Loading…