Tetrahydrofuran → 2-Methyl-5-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridine

HRID 1691305Notes

Reaction equation

O1CCCC1.[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[N:12][CH:13]=1)#[CH:7].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](Cl)=[N:31][OH:32])=[CH:25][CH:24]=1.C(N(CC)CC)C>O>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[O:32][N:31]=[C:30]([CH2:29][C:26]3[CH:25]=[CH:24][C:23]([CH2:22][O:21][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=4)=[CH:28][CH:27]=3)[CH:7]=2)=[CH:13][N:12]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a tetrahydrofuran (2 mL) solution of 5-ethynyl-2-methyl-pyridine (10 mg, 85 μmol) described in Manufacturing Example 190-1-1 were added 4-(pyridin-2-yloxymethyl)phenyl-acetohydroximoyl chloride (31 mg, 0.11 mmol) described in Manufacturing Example 2-1-5 and triethylamine (18 μL, 0.13 mmol), which was stirred for 2 hours and 30 minutes at 50° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrated was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (14 mg, 46%).

Workup

extractionwhich was extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrated was concentrated under a reduced pressure
customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-add2cab18ed54c09a54617a67f06cca1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153662B2

Reaction notes

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