4-Fluorophenol → 7-(4-Fluorophenoxy)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazole

HRID 509458Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[C:19]3[CH2:20][CH2:21][CH2:22][CH:23]([OH:24])[C:18]=3[O:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[F:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCOC(C)=O>[F:25][C:26]1[CH:31]=[CH:30][C:29]([O:24][CH:23]2[C:18]3[O:17][N:16]=[C:15]([C:5]4[CH:6]=[CH:7][C:8]([N:9]5[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]5)=[C:3]([O:2][CH3:1])[CH:4]=4)[C:19]=3[CH2:20][CH2:21][CH2:22]2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazol-7-ol (48 mg, 0.149 mmol) in THF (1.0 mL) was added 4-flurophenol (23 mg, 0.2 mmol), Ph3P (58 mg, 0.22 mmol) and DEAD (39 mg, 0.22 mmol). The reaction mixture was stirred over night at 50° C. The reaction mixture cooled, diluted with EtOAc, washed with water and brine, dried over MgSO4 and concentrated. The crude product was purified by preparative TLC using 5% MeOH in DCM as solvent to afford 27 mg of the title product.

Workup

temperatureThe reaction mixture cooled
washwashed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude product was purified by preparative TLC

Sources & evidence

ORD record: ord-b43af41842274b0583e8ac2ffc2ca707
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096582B2

Reaction notes

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