2-Pyridinemethanamine → HCID 11681859, compound

HRID 215985Notes

Reaction equation

HRID 215985 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]2[S:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:3]=12.[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>CN1C(=O)CCC1.O.C(Cl)Cl>[Cl:8][C:6]1[N:5]=[C:4]2[S:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:3]2=[C:2]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:7]=1

Participants

6

Reactant 2

HCID 195092-PyridinemethanamineHCID 86607126HCID 86607126, compound

Product 1

HCID 11681859HCID 11681859, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4,6-dichloro-3-phenyl-thieno[2,3-b]pyridine (400 mg, 1.43 mmol) and 2-aminomethylpyridine (294 μl, 1.86 mmol) in NMP (1 ml) were heated in the microwave at 200° C. for 1 h. The reaction was diluted with water (30 ml) and DCM (30 ml). The DCM layer was separated and washed with water (6×50 ml), dried (Na2SO4), and concentrated. The residue was columned on silica, eluting (EtOAc/Hexane 0-100%). The first isolated fraction gave (6-chloro-3-phenyl-thieno[2,3-b]pyridin-4-yl)-pyridin-2-ylmethyl-amine (19) as colourless crystals. Yield=288 mg (57.3%). The second isolated fraction gave (4-Chloro-3-phenyl-thieno[2,3-b]pyridin-6-yl)-pyridin-2-ylmethyl-amine (20) as an orange oil. Yield=24 mg (4.7%).

Workup

  1. customThe DCM layer was separated
  2. washwashed with water (6×50 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. washeluting (EtOAc/Hexane 0-100%)

Sources & evidence

ORD record
ord-a34ddd4234da468298ca20a34efbe8d8
Source dataset
uspto-grants-2012_06
Patent number
US08193215B2

Reaction notes

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