Potassium tert-butoxide → 8,10-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol

HRID 1513928Notes

Reaction equation

Cl.[OH:2][CH:3]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[CH:26][CH:25]=1)[C:4]1[C:13]([C:14]2[C:19]([F:20])=[CH:18][C:17]([F:21])=[CH:16][C:15]=2F)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([OH:23])=[CH:9]2.CC(C)([O-])C.[K+]>CN(C=O)C>[F:21][C:17]1[CH:16]=[C:15]2[C:14](=[C:19]([F:20])[CH:18]=1)[C:13]1[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:23])[CH:7]=[CH:6]3)[CH:3]([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)=[CH:28][CH:29]=1)[O:2]2

Participants

Conditions

Temperature: 50 °C

Procedure

Dissolve 5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2,4,6-trifluoro-phenyl)-naphthalen-2-ol hydrochloride (730 mg, 1.4 mmol) and potassium tert-butoxide (5.36 mg, 4.8 mmol) in dry DMF (25 mL) and heat at 50° C. for 10 minutes. Cool reaction and pour onto ice/ethyl acetate. Separate organic layer and wash with 10% aqueous lithium chloride. Dry, filter, and concentrate in vacuo. Purify by silica gel chromatography using a 1-6% gradient of methanol in dichloromethane to yield 532 mg (76%) of the title compound.

Workup

temperatureCool
customreaction
additionpour onto ice/ethyl acetate
washSeparate organic layer and wash with 10% aqueous lithium chloride
customDry
filtrationfilter
concentrationconcentrate in vacuo
customPurify by silica gel chromatography

Sources & evidence

ORD record: ord-52f3cb81590c4b718a78d6fde15c213b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217032B2

Reaction notes

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