Diethylamine → 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide

HRID 529390Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:6]([CH:10]=1)[C:7]([N:21]([CH2:22][CH3:23])[CH2:19][CH3:20])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 5-bromo-2-(6-chloropyridin-3-yloxy)benzoic acid (1.28 kg, 4.44 mol), diethylamine (461 mL, 4.44 mol), HOBT (600 g, 4.44 mol), DIPEA (1.547 L, 8.88 mol) in anhydrous DCM (8 L) was cooled to 0° C. EDCI (851.2 g, 4.44 mol) was added to the reaction mixture and it was stirred at 0° C. for 30 minutes and then at RT overnight. The reaction mixture was sequentially washed with aqueous NaHCO3, brine and water before being dried over MgSO4. Filtration and concentrated under reduced pressure provided a residue that was purified by silica gel chromatography (5-20% EtOAc in hexane) to provide 950 g of 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide.

Workup

customat RT
customovernight
washThe reaction mixture was sequentially washed with aqueous NaHCO3, brine and water
dry with materialbefore being dried over MgSO4
filtrationFiltration
concentrationconcentrated under reduced pressure
customprovided a residue that
customwas purified by silica gel chromatography (5-20% EtOAc in hexane)

Sources & evidence

ORD record: ord-69a15350616049f7a29ee52c96070fc0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346827B2

Reaction notes

Loading…