Potassium Carbonate → HCID 136343985, compound

HRID 1050745Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][S:13][C:9]2=[C:10](Br)[N:11]=1)=[O:5])[CH3:2].[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][S:13][C:9]2=[C:10]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 7-bromo-4-hydroxy-3-phenyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (53 mg, 0.139 mmol), Pd(PPh3)4 (16.1 mg, 0.0139 mmol), 4-fluorophenylboronic acid (29.3 mg, 0.209 mmol), K2CO3 (57.8 mg, 0.418 mmol), and 1,4-dioxane (1.39 mL) was heated at 140° C. in a microwave oven with stirring for 5 min. After cooling to r. t., the mixture was filtered and the filter cake was washed with CH2Cl2. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel. Elution with 0-20% EtOAc/CH2Cl2, gave the title compound as a white solid (27.6 mg): MS (m/z) 395.2 (M+1).

Workup

temperatureAfter cooling
filtration, the mixture was filtered
washthe filter cake was washed with CH2Cl2
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by flash column chromatography on silica gel
washElution with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record: ord-9c6d997457214a6e8c74f1fc08e32482
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09387200B2

Reaction notes

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