3-Hydroxybenzenethiol → 3-(2-Fluoro-3-aminobenzyl)-7-mercapto-4-methyl-2-oxo-2H-1-benzopyran

HRID 599844Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C([O:11][C:12](=O)[CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[C:19]=1[F:25])[C:14](=O)[CH3:15])C>O>[F:25][C:19]1[C:20]([NH2:24])=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][C:13]1[C:12](=[O:11])[O:1][C:2]2[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][C:7]=2[C:14]=1[CH3:15]

Participants

Conditions

Temperature: 70 °C

Procedure

152 mg (1.21 mmol) of 3-hydroxy-benzenethiol and 153 mg (0.60 mmol) of 2-(2-fluoro-3-aminobenzyl)-3-oxobutanoic acid ethyl ester were added to polyphosphoric acid (6 g), and the mixture was stirred and heated at 70° C. for 2.5 hours. Water was then added to the reaction mixture, and the precipitated solid was filtered out. The obtained solid was purified by silica gel column chromatography (dichloromethane:methanol=50:1 to 20:1) to yield 12 mg (1%) of compound 5d-0-4S1 as a pale yellow powder.

Workup

filtrationthe precipitated solid was filtered out
customThe obtained solid was purified by silica gel column chromatography (dichloromethane:methanol=50:1 to 20:1)

Sources & evidence

ORD record: ord-1a44b38a168940e2a6aea557aefe29b0
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897792B2

Reaction notes

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