Potassium Carbonate → Ethyl 6-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)picolinate

HRID 2356602

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[C:30]([F:36])[CH:29]=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:32][C:31]2[CH:34]=[CH:35][C:28]([Cl:27])=[CH:29][C:30]=2[F:36])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of ethyl 6-[(5-chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylate (92 mg, 0.31 mmol), potassium carbonate (109 mg, 2.5 equivalents) and 4-chloro-2-fluorobenzyl bromide (78 mg, 1.1 equivalents) in acetone (˜6 ml) was heated at 50° C. for 3-4 hours until there was no more SM (starting material). Cooled down, filtered off and washed with acetone. LC/MS okay, Rt4.05. Purified by SPE, product came off with ˜20% ethyl acetate in iso-hexane. 108 mg of a white solid. Rt=4.05 [MH+] 434, 437.

Workup

temperatureCooled down
filtrationfiltered off
washwashed with acetone
customPurified by SPE, product

Sources & evidence

ORD record: ord-1767e321d4734fb3bbc95fa506276705
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759369B2

Linked notes

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