2,6-Dichloropyridine → HCID 86602126, compound

HRID 1726125Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH:16]([OH:27])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31](Cl)[N:30]=1>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][CH:13]([CH:16]([O:27][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([Cl:28])[N:30]=2)[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=2)[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of NaH (60% in mineral oil, 56 mg, 1.4 mmol) in DMF (2.3 mL) was added 4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (250 mg, 0.696 mmol) followed by 2,6-dichloropyridine (309 mg, 2.09 mmol). The mixture was heated to 90° C. for 2 h then concentrated in vacuo. Aqueous work-up and purification gave 4-[(6-chloro-pyridin-2-yloxy)-(4-trifluoromethyl-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester as a colourless foam (313 mg, 95%).

Workup

concentrationthen concentrated in vacuo
customAqueous work-up and purification

Sources & evidence

ORD record: ord-8b4eb7e505f144f7ba223963cf20f00b
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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