Piperazine → HCID 58996617, compound

HRID 1592729Notes

Reaction equation

Br[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>>[N:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=2[N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:6]=1

Participants

Reactant 2

HCID 4837Piperazine

HCID 12673494HCID 12673494, compound

Product 1

HCID 58996617HCID 58996617, compound

Procedure

2-Bromophenol (355 mg, 2.05 mmol), 3-pyridyl-boronic acid (500 mg, 4.1 mmol), copper acetate (745 mg, 4.1 mmol) and pyridine (3.3 mL, 41 mmol) were added to dichloromethane (41 mL) and stirred for about 48 hours under air. The reaction was diluted with water (50 mL) and the layers separated. The organic layer was washed with 5N NaOH. The organic layer was concentrated, and chromatographed on silica gel (MeOH/dichloromethane) to yield 3-(2-bromo-phenoxy)-pyridine (30 mg, 6%) as a yellow oil. MS found 249.1 M+1. 3-(2-Bromo-phenoxy)-pyridine was coupled to piperazine using the Buchwald chemistry described in preparation 1A to afford the title compound. LRMS (ESI+): 256.1 (M+1)

Sources & evidence

ORD record: ord-0ab082dec8894a2eb60a093eb57fecb2
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291619B2

Reaction notes

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