1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide

HRID 931538Notes

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.C1C=CC2N(O)N=NC=2C=1.[CH3:29][CH2:30][N:31](C(C)C)[CH:32](C)[CH3:33].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:31]([CH2:32][CH3:33])[CH2:30][CH3:29])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of compound 5-bromo-2-(6-chloropyridin-3-yloxy)benzoic acid (1.28 Kg, 4.44 mol), DEA (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. and EDCI (851.2 g, 4.44 mol, 1 eq) was added. The mixture was stirred at 0° C. for 30 minutes and then at RT overnight. The reaction mixture was washed with an aqueous, saturated solution of NaHCO3, brine and water. The organic phase was separated, dried over MgSO4 and concentrated under reduced pressure. The resulting crude mixture was purified by silica gel chromatography (5 to 20% ethyl acetate in hexane) to afford 950 g of 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethylbenzamide as a yellow oil.

Workup

customat RT
customovernight
washThe reaction mixture was washed with an aqueous, saturated solution of NaHCO3, brine and water
customThe organic phase was separated
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe resulting crude mixture was purified by silica gel chromatography (5 to 20% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-6add77cde52e4e9ab26f93a7d2c32676
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296759B2

Reaction notes

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