Dimethylformamide → 3-Pyridylthio-2-phenylbenzoic acid tert-butyl ester

HRID 2121211Notes

Reaction equation

[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([N+]([O-])=O)=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].Cl.COC(=O)[C@H:27]([CH2:44][CH2:45][S:46]C)NC(=O)C1C=CC(N)=CC=1C1C=CC=CC=1.[CH3:49][N:50]([CH:52]=O)C>C(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:46][C:45]2[CH:49]=[N:50][CH:52]=[CH:27][CH:44]=2)[C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture in DMF (2 mL) of 4-nitro-2-phenylbenzoic acid tert-butyl ester (403 mg, 1.35 mmol), prepared by esterification of 4-nitro-2-phenylbenzoic acid (compound 8, step B), and 3-thiopyridine sodium salt (224 mg, 1.68 mmol), prepared as in 232C, was stirred at 100° C. for 60 hours. The reaction mixture was cooled to ambient temperature and diluted with saturated aqueous sodium bicarbonate. The mixture was extracted with ether (3×). The combined ether extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to give a brown oil. Chromatography on silica gel (10% ethyl acetate-hexanes) gave 3-pyridylthio-2-phenylbenzoic acid tert-butyl ester as a colorless oil (248 mg, 51%).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
extractionThe mixture was extracted with ether (3×)
dry with materialThe combined ether extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give a brown oil

Sources & evidence

ORD record: ord-1c68836943cb46079fe6d6056f32147f
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693123B2

Reaction notes

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