Water → HCID 46191488, compound

HRID 1941762Notes

Reaction equation

[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].O.[F:7][C:8]([F:19])([F:18])[C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.[C:20](=[O:23])(O)[O-].[Na+].CN([CH:28]=[O:29])C>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>[CH3:1][S:2]([NH:5][C:9]1[CH:14]=[CH:13][C:12]([C:12]2[CH:13]=[CH:14][C:9]([C:8]([F:19])([F:18])[F:7])=[CH:10][CH:11]=2)=[CH:11][C:10]=1[C:20]([O:29][CH3:28])=[O:23])(=[O:4])=[O:3]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methane sulfonamide (308 mg, 1 mmol) in DMF:H2O (10 mL; 9:1), 4-trifluoromethyl phenylboronic acid (227 mg, 1.2 mmol) was added followed by sodium bicarbonate (252 mg, 3 mmol) and stirred under nitrogen for 5 min. To the reaction mixture Pd(PPh3)4 (55 mg, 0.05 mmol) was added and heated at 90° C. for 90 min. The reaction mixture was cooled, filtered through celite, washed with EtoAc (50 mL). The combined organics were washed with water, brine, dried over Na2SO4 and concentrated. The product (180 mg, 49%) was purified by preparative TLC by eluting with CH2Cl2.to give methyl 4-[(methylsulfonyl)amino]-4′-(trifluoromethyl)biphenyl-3-carboxylate, PT-121.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered through celite
washwashed with EtoAc (50 mL)
washThe combined organics were washed with water, brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe product (180 mg, 49%) was purified by preparative TLC
washby eluting with CH2Cl2

Sources & evidence

ORD record: ord-87bef126f5b042f6944b98adc647a3d3
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389500B2

Reaction notes

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