3-Bromopyridine → HCID 13304847, compound

HRID 2179284Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1>>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1

Participants

Reactant 2

HCID 122863-Bromopyridine

HCID 310183-Pyridinemethanamine

Product 1

HCID 13304847HCID 13304847, compoundYield 83%

Procedure

Using the general procedure, 3-bromopyridine (96 μL, 1.0 mmol) was coupled with 3-(aminomethyl)pyridine (153 μL, 1.5 mmol) at 90° C. for 20 h. Purification of the crude product by column chromatography on silica gel using dichloromethane(saturated with ammonia)/methanol (15:1) as eluent afforded the desired product as a light yellow liquid (153 mg, 83% yield). Rf=0.4 (dichloromethane(saturated with ammonia)/methanol=10:1).

Workup

customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record: ord-7e3c9ebaef5b44e9aa653898084a6746
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067955B2

Reaction notes

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