Water → 2-Aminocarbonylamino-5-(4-vinylphenyl)pyrrole-3-carboxamide

HRID 1011579Notes

Reaction equation

[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].C(=O)([O-])O.[Na+].[CH:25](B1OC(C)(C)C(C)(C)O1)=[CH2:26].O>[Cl-].[Na+].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.O1CCOCC1>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][C:16]([CH:25]=[CH2:26])=[CH:15][CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

Conditions

Temperature: 95 °C

Procedure

2-Aminocarbonylamino-5-(4-bromophenyl)pyrrole-3-carboxamide (Compound No. 1-1, 80 mg, 0.25 mmol), sodium hydrogencarbonate (52 mg, 0.62 mmol), vinylboronic acid pinacol ester (63 μL, 0.37 mmol) and tetrakis(triphenylphosphine)palladium(0) (14 mg, 0.012 mmol) in mixed solvent (4 mL), which consists of water and 1,4-dioxane (1:3), were stirred overnight at 95° C. The brine (10 mL) was added to the reaction solution, extracted with ethyl acetate (10 mL), and then the organic layer was dried over magnesium sulfate. The layer was filtered with celite and the solvent was removed under reduced pressure. The obtained solid was washed with diethyl ether (2 mL), and dried under reduced pressure to give the target compound (22 mg) as a pale brown solid (Yield 33%).

Workup

extractionextracted with ethyl acetate (10 mL)
dry with materialthe organic layer was dried over magnesium sulfate
filtrationThe layer was filtered with celite
customthe solvent was removed under reduced pressure
washThe obtained solid was washed with diethyl ether (2 mL)
customdried under reduced pressure

Sources & evidence

ORD record: ord-5d0509ea1ec4456f82b67e68897f1655
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977371B2

Reaction notes

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