Ethanol → HCID 67237886, compound

HRID 2363155Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:23])[C:17]=1[NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH2:5][NH:6][C:7]([C:9]1[S:10][C:11](Br)=[CH:12][CH:13]=1)=[O:8].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1(C)C=CC=CC=1.CCOC(C)=O.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>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:23])[C:17]=1[NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([C:29]2[CH:30]=[CH:31][C:26]([C:25]([F:36])([F:35])[F:24])=[CH:27][CH:28]=2)=[CH:12][CH:13]=1)=[O:8]

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of 5-bromo-thiophene-2-carboxylic acid 3,5-difluoro-4-methanesulfonylamino-benzylamide (100 mg, 0.235 mmol), Pd(PPh3)4 (4.1 mg, 0.0035 mmol), and 4-trifluoromethyl phenyl boronic acid (53.5 mg, 0.282 mmol) in toluene (1 mL) was added 2N—Na2CO3 (0.5 mL)/EtOH (0.5 mL). The mixture was stirred 3 hours at 110° C. and was diluted with EtOAc. The mixture was washed with 1N HCl, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give title compound (90 mg, 78%).

Workup

washThe mixture was washed with 1N HCl, water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane)

Sources & evidence

ORD record: ord-1e5707ca51e846eaae92680296436f02
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691855B2

Reaction notes

Loading…