Dimethylformamide → 3-Phenyl-2-[4-[3-(1-pyrrolidinyl)propoxy]phenyl]-1,4-benzoxathiin

HRID 1696685Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br.BrC[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CN(C=O)C.[C:23]1([C:29]2[S:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[O:31][C:30]=2[C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)(=O)C>[C:23]1([C:29]2[S:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[O:31][C:30]=2[C:39]2[CH:40]=[CH:41][C:42]([O:45][CH2:15][CH2:16][CH2:17][N:12]3[CH2:11][CH2:10][CH2:14][CH2:13]3)=[CH:43][CH:44]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (83 mg) and 1-(3-bromopropyl)piperidine hydrobromide (54.6 mg) were added to a DMF (3 mL) solution of 4-(3-phenyl-1,4-benzoxathiin-2-yl)phenol (63.7 mg, 0.2 mmol) obtained in Reference Example 1-1, and stirred at 80° C. for 8 hours. The reaction liquid was restored to room temperature, diluted with ethyl acetate, and extracted with distilled water. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer silica gel column chromatography (chloroform:methanol=9:1) to obtain the entitled compound (43.7 mg, 51%) as a yellow oil.

Workup

customobtained in Reference Example 1-1
customThe reaction liquid
customwas restored to room temperature
extractionextracted with distilled water
dry with materialThe organic layer was dried with magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by preparative thin-layer silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record: ord-faf5a1f3c14d4aeaabe3000da1f38c21
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163770B2

Reaction notes

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